Ingredient	UNII	CAS	InChI Key
Harmaline hydrochloride	64056X913V	363-11-1	PULNGKOFHCQQQA-UHFFFAOYSA-N
Harmaline hydrochloride dihydrate	5B4DGH2M9R	6027-98-1	LCEKUHFBUFUSSY-UHFFFAOYSA-N

Categories

UNII

CN58I4TOET

CAS number

304-21-2

Weight

Average: 214.2631
Monoisotopic: 214.11061308

Chemical Formula

C₁₃H₁₄N₂O

InChI Key

RERZNCLIYCABFS-UHFFFAOYSA-N

InChI

InChI=1S/C13H14N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7,15H,5-6H2,1-2H3

IUPAC Name

7-methoxy-1-methyl-3H,4H,9H-pyrido[3,4-b]indole

SMILES

COC1=CC2=C(C=C1)C1=C(N2)C(C)=NCC1

Pharmacology

Indication

Not Available

Pharmacodynamics

Not Available

Mechanism of action

Target	Actions	Organism
UHistamine N-methyltransferase	inhibitor	Human

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Harmaline
Harmalol

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction	Drug group
2,5-Dimethoxy-4-ethylamphetamine	The risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Harmaline.	Experimental, Illicit
2,5-Dimethoxy-4-ethylthioamphetamine	The risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Harmaline.	Experimental
3,4-Methylenedioxyamphetamine	The risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Harmaline.	Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamine	The risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Harmaline.	Experimental, Illicit
4-Methoxyamphetamine	Harmaline may increase the hypertensive activities of 4-Methoxyamphetamine.	Experimental, Illicit
5-methoxy-N,N-dimethyltryptamine	The metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Harmaline.	Experimental, Illicit
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline	7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypertensive activities of Harmaline.	Experimental
Abediterol	The risk or severity of adverse effects can be increased when Harmaline is combined with Abediterol.	Investigational
Acarbose	Harmaline may increase the hypoglycemic activities of Acarbose.	Approved, Investigational
Acebutolol	Harmaline may increase the hypotensive activities of Acebutolol.	Approved, Investigational
Alaproclate	The risk or severity of adverse effects can be increased when Alaproclate is combined with Harmaline.	Experimental
Albiglutide	Harmaline may increase the hypoglycemic activities of Albiglutide.	Approved
Aldesleukin	Harmaline may increase the orthostatic hypotensive activities of Aldesleukin.	Approved
Alfentanil	The risk or severity of adverse effects can be increased when Alfentanil is combined with Harmaline.	Approved, Illicit
Aliskiren	Harmaline may increase the hypotensive activities of Aliskiren.	Approved, Investigational
Almotriptan	The serum concentration of Almotriptan can be increased when it is combined with Harmaline.	Approved, Investigational
Alogliptin	Harmaline may increase the hypoglycemic activities of Alogliptin.	Approved
Alphacetylmethadol	The risk or severity of adverse effects can be increased when Alphacetylmethadol is combined with Harmaline.	Experimental, Illicit
Alphaprodine	The risk or severity of adverse effects can be increased when Alphaprodine is combined with Harmaline.	Illicit
Alprenolol	Harmaline may increase the hypotensive activities of Alprenolol.	Approved, Withdrawn
Altretamine	Altretamine may increase the orthostatic hypotensive activities of Harmaline.	Approved
Ambrisentan	Harmaline may increase the hypotensive activities of Ambrisentan.	Approved, Investigational
Amikacin	The risk or severity of adverse effects can be increased when Harmaline is combined with Amikacin.	Approved, Investigational, Vet Approved
Amineptine	Harmaline may increase the serotonergic activities of Amineptine.	Illicit, Withdrawn
Amiodarone	Harmaline may increase the orthostatic hypotensive activities of Amiodarone.	Approved, Investigational
Amitriptyline	Harmaline may increase the serotonergic activities of Amitriptyline.	Approved
Amitriptylinoxide	Harmaline may increase the serotonergic activities of Amitriptylinoxide.	Approved, Investigational
Amlodipine	Harmaline may increase the hypotensive activities of Amlodipine.	Approved
Amoxapine	Harmaline may increase the serotonergic activities of Amoxapine.	Approved
Amphetamine	The risk or severity of adverse effects can be increased when Amphetamine is combined with Harmaline.	Approved, Illicit, Investigational
Apomorphine	The metabolism of Apomorphine can be decreased when combined with Harmaline.	Approved, Investigational
Apraclonidine	The risk or severity of adverse effects can be increased when Harmaline is combined with Apraclonidine.	Approved
Arbutamine	The risk or severity of adverse effects can be increased when Harmaline is combined with Arbutamine.	Approved
Arformoterol	The risk or severity of adverse effects can be increased when Harmaline is combined with Arformoterol.	Approved, Investigational
Atenolol	Harmaline may increase the hypotensive activities of Atenolol.	Approved
Atomoxetine	Harmaline may increase the central neurotoxic activities of Atomoxetine.	Approved
Atropine	The risk or severity of hypertension can be increased when Harmaline is combined with Atropine.	Approved, Vet Approved
Bambuterol	The risk or severity of adverse effects can be increased when Harmaline is combined with Bambuterol.	Approved, Investigational
Barnidipine	Harmaline may increase the orthostatic hypotensive activities of Barnidipine.	Approved
Benazepril	Harmaline may increase the hypotensive activities of Benazepril.	Approved, Investigational
Bendroflumethiazide	Harmaline may increase the hypotensive activities of Bendroflumethiazide.	Approved
Benmoxin	Benmoxin may increase the hypertensive activities of Harmaline.	Withdrawn
Benzphetamine	Harmaline may increase the hypertensive activities of Benzphetamine.	Approved, Illicit
Benzyl alcohol	The risk or severity of adverse effects can be increased when Benzyl alcohol is combined with Harmaline.	Approved
Bepridil	Harmaline may increase the hypotensive activities of Bepridil.	Approved, Withdrawn
Betahistine	The serum concentration of Betahistine can be increased when it is combined with Harmaline.	Approved, Investigational
Betaxolol	Harmaline may increase the hypotensive activities of Betaxolol.	Approved, Investigational
Bethanidine	Harmaline may increase the hypotensive activities of Bethanidine.	Approved
Bezafibrate	The risk or severity of adverse effects can be increased when Harmaline is combined with Bezafibrate.	Approved, Investigational
Bietaserpine	Harmaline may increase the hypotensive activities of Bietaserpine.	Experimental
Bimatoprost	Harmaline may increase the hypotensive activities of Bimatoprost.	Approved, Investigational
Bisoprolol	Harmaline may increase the hypotensive activities of Bisoprolol.	Approved
Bitolterol	The risk or severity of adverse effects can be increased when Harmaline is combined with Bitolterol.	Withdrawn
Bosentan	Harmaline may increase the hypotensive activities of Bosentan.	Approved, Investigational
Botulinum Toxin Type B	The risk or severity of adverse effects can be increased when Harmaline is combined with Botulinum Toxin Type B.	Approved, Investigational
BQ-123	Harmaline may increase the hypotensive activities of BQ-123.	Investigational
Bretylium	Harmaline may increase the hypotensive activities of Bretylium.	Approved
Brexpiprazole	The metabolism of Brexpiprazole can be decreased when combined with Harmaline.	Approved, Investigational
Brimonidine	The risk or severity of adverse effects can be increased when Harmaline is combined with Brimonidine.	Approved
Brofaromine	Harmaline may increase the hypertensive activities of Brofaromine.	Experimental
Bromocriptine	The metabolism of Bromocriptine can be decreased when combined with Harmaline.	Approved, Investigational
Brompheniramine	The risk or severity of adverse effects can be increased when Brompheniramine is combined with Harmaline.	Approved
Bupranolol	Harmaline may increase the hypotensive activities of Bupranolol.	Approved
Buprenorphine	The risk or severity of adverse effects can be increased when Buprenorphine is combined with Harmaline.	Approved, Illicit, Investigational, Vet Approved
Bupropion	The risk or severity of adverse effects can be increased when Harmaline is combined with Bupropion.	Approved
Buspirone	The risk or severity of adverse effects can be increased when Harmaline is combined with Buspirone.	Approved, Investigational
Butorphanol	The risk or severity of adverse effects can be increased when Butorphanol is combined with Harmaline.	Approved, Illicit, Vet Approved
Butriptyline	Harmaline may increase the serotonergic activities of Butriptyline.	Approved
Cabergoline	The metabolism of Cabergoline can be decreased when combined with Harmaline.	Approved
Cadralazine	Harmaline may increase the hypotensive activities of Cadralazine.	Experimental
Cafedrine	Harmaline may increase the hypotensive activities of Cafedrine.	Investigational
Canagliflozin	Harmaline may increase the hypoglycemic activities of Canagliflozin.	Approved
Candesartan	Harmaline may increase the hypotensive activities of Candesartan.	Experimental
Candesartan cilexetil	Harmaline may increase the hypotensive activities of Candesartan cilexetil.	Approved
Candoxatril	Harmaline may increase the hypotensive activities of Candoxatril.	Experimental
Captopril	Harmaline may increase the hypotensive activities of Captopril.	Approved
Carbamazepine	The risk or severity of adverse effects can be increased when Carbamazepine is combined with Harmaline.	Approved, Investigational
Carfentanil	The risk or severity of adverse effects can be increased when Carfentanil is combined with Harmaline.	Illicit, Investigational, Vet Approved
Cariprazine	The metabolism of Cariprazine can be decreased when combined with Harmaline.	Approved, Investigational
Caroxazone	Caroxazone may increase the hypertensive activities of Harmaline.	Withdrawn
Carteolol	Harmaline may increase the hypotensive activities of Carteolol.	Approved
Carvedilol	Harmaline may increase the hypotensive activities of Carvedilol.	Approved, Investigational
Celiprolol	Harmaline may increase the hypotensive activities of Celiprolol.	Approved, Investigational
Cetirizine	The risk or severity of adverse effects can be increased when Cetirizine is combined with Harmaline.	Approved
Chlorothiazide	Harmaline may increase the hypotensive activities of Chlorothiazide.	Approved, Vet Approved
Chlorphenamine	The risk or severity of adverse effects can be increased when Chlorphenamine is combined with Harmaline.	Approved
Chlorphentermine	The risk or severity of adverse effects can be increased when Chlorphentermine is combined with Harmaline.	Illicit, Withdrawn
Chlorpropamide	Harmaline may increase the hypoglycemic activities of Chlorpropamide.	Approved, Investigational
Chlorthalidone	Harmaline may increase the hypotensive activities of Chlorthalidone.	Approved
Cicletanine	Harmaline may increase the hypotensive activities of Cicletanine.	Investigational
Cilazapril	Harmaline may increase the hypotensive activities of Cilazapril.	Approved
Cilnidipine	Harmaline may increase the orthostatic hypotensive activities of Cilnidipine.	Approved, Investigational
Cinitapride	The metabolism of Cinitapride can be decreased when combined with Harmaline.	Approved, Investigational
Cirazoline	Harmaline may increase the hypertensive activities of Cirazoline.	Experimental
Citalopram	The risk or severity of adverse effects can be increased when Citalopram is combined with Harmaline.	Approved
Clemastine	Harmaline may increase the anticholinergic activities of Clemastine.	Approved, Investigational
Clenbuterol	The risk or severity of adverse effects can be increased when Harmaline is combined with Clenbuterol.	Approved, Investigational, Vet Approved
Clevidipine	Harmaline may increase the orthostatic hypotensive activities of Clevidipine.	Approved, Investigational
Clindamycin	The risk or severity of adverse effects can be increased when Harmaline is combined with Clindamycin.	Approved, Vet Approved
Clomipramine	Harmaline may increase the serotonergic activities of Clomipramine.	Approved, Investigational, Vet Approved
Clonidine	Harmaline may increase the hypertensive activities of Clonidine.	Approved
Cloranolol	Harmaline may increase the hypotensive activities of Cloranolol.	Experimental
Codeine	The risk or severity of adverse effects can be increased when Codeine is combined with Harmaline.	Approved, Illicit
Cryptenamine	Harmaline may increase the hypotensive activities of Cryptenamine.	Approved
Cyclobenzaprine	Cyclobenzaprine may increase the serotonergic activities of Harmaline.	Approved
Cyclopenthiazide	Harmaline may increase the hypotensive activities of Cyclopenthiazide.	Experimental
Cyclosporine	The risk or severity of adverse effects can be increased when Harmaline is combined with Cyclosporine.	Approved, Investigational, Vet Approved
Cyclothiazide	Harmaline may increase the hypotensive activities of Cyclothiazide.	Approved
Cyproheptadine	Harmaline may increase the anticholinergic activities of Cyproheptadine.	Approved
Dapagliflozin	Harmaline may increase the orthostatic hypotensive activities of Dapagliflozin.	Approved
Dapoxetine	The risk or severity of adverse effects can be increased when Dapoxetine is combined with Harmaline.	Investigational
Debrisoquin	Harmaline may increase the hypotensive activities of Debrisoquin.	Approved, Investigational
Delapril	Harmaline may increase the hypotensive activities of Delapril.	Investigational
Deserpidine	Harmaline may increase the hypotensive activities of Deserpidine.	Approved
Desipramine	Harmaline may increase the serotonergic activities of Desipramine.	Approved, Investigational
Desvenlafaxine	Harmaline may increase the serotonergic activities of Desvenlafaxine.	Approved, Investigational
Deutetrabenazine	The risk or severity of adverse effects can be increased when Harmaline is combined with Deutetrabenazine.	Approved, Investigational
Dexbrompheniramine	The risk or severity of adverse effects can be increased when Dexbrompheniramine is combined with Harmaline.	Approved
Dexmethylphenidate	Harmaline may increase the hypertensive activities of Dexmethylphenidate.	Approved, Investigational
Dexniguldipine	Harmaline may increase the hypotensive activities of Dexniguldipine.	Experimental
Dextroamphetamine	The risk or severity of adverse effects can be increased when Dextroamphetamine is combined with Harmaline.	Approved, Illicit
Dextromethorphan	The risk or severity of serotonin syndrome can be increased when Harmaline is combined with Dextromethorphan.	Approved
Dextromoramide	The risk or severity of adverse effects can be increased when Dextromoramide is combined with Harmaline.	Experimental, Illicit
Dextropropoxyphene	The risk or severity of adverse effects can be increased when Dextropropoxyphene is combined with Harmaline.	Approved, Illicit, Investigational, Withdrawn
Dezocine	The risk or severity of adverse effects can be increased when Dezocine is combined with Harmaline.	Approved, Investigational
Diazoxide	Harmaline may increase the hypotensive activities of Diazoxide.	Approved
Dibenzepin	Harmaline may increase the serotonergic activities of Dibenzepin.	Experimental
Diethylnorspermine	Harmaline may increase the hypotensive activities of Diethylnorspermine.	Investigational
Diethylpropion	The risk or severity of adverse effects can be increased when Harmaline is combined with Diethylpropion.	Approved, Illicit
Dihydralazine	Harmaline may increase the hypotensive activities of Dihydralazine.	Approved, Investigational
Dihydrocodeine	The risk or severity of adverse effects can be increased when Dihydrocodeine is combined with Harmaline.	Approved, Illicit
Dihydroergotamine	The metabolism of Dihydroergotamine can be decreased when combined with Harmaline.	Approved, Investigational
Dihydroetorphine	The risk or severity of adverse effects can be increased when Dihydroetorphine is combined with Harmaline.	Experimental, Illicit
Dihydromorphine	The risk or severity of adverse effects can be increased when Dihydromorphine is combined with Harmaline.	Experimental, Illicit
Diltiazem	Harmaline may increase the hypotensive activities of Diltiazem.	Approved, Investigational
Dimenhydrinate	The risk or severity of adverse effects can be increased when Dimenhydrinate is combined with Harmaline.	Approved
Dimetacrine	Harmaline may increase the serotonergic activities of Dimetacrine.	Approved, Withdrawn
Diphenhydramine	The risk or severity of adverse effects can be increased when Diphenhydramine is combined with Harmaline.	Approved, Investigational
Diphenoxylate	The risk or severity of adverse effects can be increased when Diphenoxylate is combined with Harmaline.	Approved, Illicit
Dipivefrin	Harmaline may increase the hypertensive activities of Dipivefrin.	Approved
Disopyramide	Harmaline may increase the hypoglycemic activities of Disopyramide.	Approved
Disulfiram	The risk or severity of convulsion can be increased when Harmaline is combined with Disulfiram.	Approved
Dobutamine	The risk or severity of adverse effects can be increased when Harmaline is combined with Dobutamine.	Approved
Domperidone	The risk or severity of adverse effects can be increased when Harmaline is combined with Domperidone.	Approved, Investigational, Vet Approved
Dorzolamide	Harmaline may increase the hypotensive activities of Dorzolamide.	Approved
Dosulepin	Harmaline may increase the serotonergic activities of Dosulepin.	Approved
Dotarizine	The risk or severity of adverse effects can be increased when Harmaline is combined with Dotarizine.	Investigational
Doxapram	Harmaline may increase the hypertensive activities of Doxapram.	Approved, Vet Approved
Doxazosin	Harmaline may increase the hypotensive activities of Doxazosin.	Approved
Doxepin	Harmaline may increase the serotonergic activities of Doxepin.	Approved, Investigational
Doxofylline	The risk or severity of adverse effects can be increased when Harmaline is combined with Doxofylline.	Approved, Investigational
Doxylamine	Doxylamine may increase the central nervous system depressant (CNS depressant) activities of Harmaline.	Approved, Vet Approved
DPDPE	The risk or severity of adverse effects can be increased when DPDPE is combined with Harmaline.	Experimental
Drotebanol	The risk or severity of adverse effects can be increased when Drotebanol is combined with Harmaline.	Experimental, Illicit
Droxidopa	Harmaline may increase the hypertensive activities of Droxidopa.	Approved, Investigational
Dulaglutide	Harmaline may increase the hypoglycemic activities of Dulaglutide.	Approved, Investigational
Duloxetine	The risk or severity of adverse effects can be increased when Duloxetine is combined with Harmaline.	Approved
Ecgonine	The risk or severity of adverse effects can be increased when Ecgonine is combined with Harmaline.	Experimental, Illicit
Efonidipine	Harmaline may increase the hypotensive activities of Efonidipine.	Approved, Investigational
Eletriptan	The serum concentration of Eletriptan can be increased when it is combined with Harmaline.	Approved, Investigational
Empagliflozin	Harmaline may increase the hypoglycemic activities of Empagliflozin.	Approved
Enalapril	Harmaline may increase the hypotensive activities of Enalapril.	Approved, Vet Approved
Enalaprilat	Harmaline may increase the hypotensive activities of Enalaprilat.	Approved
Endralazine	Harmaline may increase the hypotensive activities of Endralazine.	Experimental
Entacapone	The risk or severity of adverse effects can be increased when Entacapone is combined with Harmaline.	Approved, Investigational
Epanolol	Harmaline may increase the hypotensive activities of Epanolol.	Experimental
Eperisone	The risk or severity of adverse effects can be increased when Harmaline is combined with Eperisone.	Approved, Investigational
Ephedra	The risk or severity of adverse effects can be increased when Harmaline is combined with Ephedra.	Approved, Nutraceutical, Withdrawn
Epinephrine	Harmaline may increase the hypertensive activities of Epinephrine.	Approved, Vet Approved
Epoprostenol	Harmaline may increase the hypotensive activities of Epoprostenol.	Approved
Eprosartan	Harmaline may increase the hypotensive activities of Eprosartan.	Approved
Ergonovine	Harmaline may increase the hypertensive activities of Ergonovine.	Approved
Ergotamine	Harmaline may increase the hypertensive activities of Ergotamine.	Approved
Escitalopram	The risk or severity of adverse effects can be increased when Escitalopram is combined with Harmaline.	Approved, Investigational
Etafedrine	The risk or severity of adverse effects can be increased when Harmaline is combined with Etafedrine.	Approved
Ethanol	Harmaline may increase the central nervous system depressant (CNS depressant) activities of Ethanol.	Approved
Ethosuximide	The risk or severity of adverse effects can be increased when Ethosuximide is combined with Harmaline.	Approved
Ethylmorphine	The risk or severity of adverse effects can be increased when Ethylmorphine is combined with Harmaline.	Approved, Illicit
Etomidate	The risk or severity of adverse effects can be increased when Etomidate is combined with Harmaline.	Approved
Etoperidone	The risk or severity of adverse effects can be increased when Etoperidone is combined with Harmaline.	Withdrawn
Etorphine	The risk or severity of adverse effects can be increased when Etorphine is combined with Harmaline.	Illicit, Vet Approved
Exenatide	Harmaline may increase the hypoglycemic activities of Exenatide.	Approved, Investigational
Felodipine	Harmaline may increase the hypotensive activities of Felodipine.	Approved, Investigational
Fenfluramine	Harmaline may increase the serotonergic activities of Fenfluramine.	Approved, Illicit, Investigational, Withdrawn
Fenoldopam	Harmaline may increase the hypotensive activities of Fenoldopam.	Approved
Fenoterol	The risk or severity of adverse effects can be increased when Harmaline is combined with Fenoterol.	Approved, Investigational
Fentanyl	The risk or severity of hypertension, serotonin syndrome, and CNS depression can be increased when Harmaline is combined with Fentanyl.	Approved, Illicit, Investigational, Vet Approved
Ferulic acid	Harmaline may increase the hypotensive activities of Ferulic acid.	Experimental
Flibanserin	The metabolism of Flibanserin can be decreased when combined with Harmaline.	Approved, Investigational
Flunarizine	The risk or severity of adverse effects can be increased when Flunarizine is combined with Harmaline.	Approved
Fluoxetine	Harmaline may increase the serotonergic activities of Fluoxetine.	Approved, Vet Approved
Fluspirilene	The risk or severity of adverse effects can be increased when Harmaline is combined with Fluspirilene.	Approved, Investigational
Fluticasone propionate	The risk or severity of adverse effects can be increased when Fluticasone propionate is combined with Harmaline.	Approved
Fluvoxamine	Harmaline may increase the serotonergic activities of Fluvoxamine.	Approved, Investigational
Formoterol	The risk or severity of adverse effects can be increased when Harmaline is combined with Formoterol.	Approved, Investigational
Fosinopril	Harmaline may increase the hypotensive activities of Fosinopril.	Approved
Frovatriptan	The serum concentration of Frovatriptan can be increased when it is combined with Harmaline.	Approved, Investigational
Furazolidone	Furazolidone may increase the hypertensive activities of Harmaline.	Approved, Investigational, Vet Approved
Furosemide	Harmaline may increase the orthostatic hypotensive activities of Furosemide.	Approved, Vet Approved
Gabapentin	The risk or severity of adverse effects can be increased when Gabapentin is combined with Harmaline.	Approved, Investigational
Gepefrine	The risk or severity of adverse effects can be increased when Gepefrine is combined with Harmaline.	Experimental
Gliclazide	Harmaline may increase the hypoglycemic activities of Gliclazide.	Approved
Glimepiride	Harmaline may increase the hypoglycemic activities of Glimepiride.	Approved
Glipizide	Harmaline may increase the hypoglycemic activities of Glipizide.	Approved, Investigational
Glyburide	Harmaline may increase the hypoglycemic activities of Glyburide.	Approved
Guanabenz	Harmaline may increase the hypotensive activities of Guanabenz.	Approved, Investigational
Guanadrel	Harmaline may increase the hypotensive activities of Guanadrel.	Approved
Guanazodine	Harmaline may increase the hypotensive activities of Guanazodine.	Experimental
Guanethidine	Harmaline may increase the hypotensive activities of Guanethidine.	Approved
Guanfacine	Harmaline may increase the hypotensive activities of Guanfacine.	Approved, Investigational
Guanoclor	Harmaline may increase the hypotensive activities of Guanoclor.	Experimental
Guanoxabenz	Harmaline may increase the hypotensive activities of Guanoxabenz.	Experimental
Guanoxan	Harmaline may increase the hypotensive activities of Guanoxan.	Experimental
Heroin	The risk or severity of adverse effects can be increased when Heroin is combined with Harmaline.	Approved, Illicit, Investigational
Hexamethonium	Harmaline may increase the hypotensive activities of Hexamethonium.	Experimental
Hexoprenaline	The risk or severity of adverse effects can be increased when Harmaline is combined with Hexoprenaline.	Approved, Withdrawn
Hydracarbazine	Hydracarbazine may increase the hypertensive activities of Harmaline.	Experimental
Hydralazine	Harmaline may increase the hypotensive activities of Hydralazine.	Approved
Hydrochlorothiazide	Harmaline may increase the hypotensive activities of Hydrochlorothiazide.	Approved, Vet Approved
Hydrocodone	Harmaline may increase the serotonergic and central nervous system depressant (CNS depressant) activities of Hydrocodone.	Approved, Illicit
Hydroflumethiazide	Harmaline may increase the hypotensive activities of Hydroflumethiazide.	Approved, Investigational
Hydromorphone	The risk or severity of adverse effects can be increased when Hydromorphone is combined with Harmaline.	Approved, Illicit
Hydroxyamphetamine	The risk or severity of adverse effects can be increased when Hydroxyamphetamine is combined with Harmaline.	Approved
Hydroxyzine	Hydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Harmaline.	Approved
Imidapril	Harmaline may increase the hypotensive activities of Imidapril.	Investigational
Imipramine	Harmaline may increase the serotonergic activities of Imipramine.	Approved
Indacaterol	The risk or severity of adverse effects can be increased when Harmaline is combined with Indacaterol.	Approved
Indalpine	The risk or severity of adverse effects can be increased when Indalpine is combined with Harmaline.	Investigational, Withdrawn
Indapamide	Harmaline may increase the hypotensive activities of Indapamide.	Approved
Indenolol	Harmaline may increase the hypotensive activities of Indenolol.	Withdrawn
Indoramin	Harmaline may increase the hypotensive activities of Indoramin.	Withdrawn
Insulin Aspart	Harmaline may increase the hypoglycemic activities of Insulin Aspart.	Approved
Insulin Detemir	Harmaline may increase the hypoglycemic activities of Insulin Detemir.	Approved
Insulin Glargine	Harmaline may increase the hypoglycemic activities of Insulin Glargine.	Approved
Insulin Glulisine	Harmaline may increase the hypoglycemic activities of Insulin Glulisine.	Approved
Insulin Human	Harmaline may increase the hypoglycemic activities of Insulin Human.	Approved, Investigational
Insulin Lispro	Harmaline may increase the hypoglycemic activities of Insulin Lispro.	Approved
Iofetamine I-123	The risk or severity of adverse effects can be increased when Iofetamine I-123 is combined with Harmaline.	Approved
Iprindole	Harmaline may increase the serotonergic activities of Iprindole.	Experimental
Iproclozide	Iproclozide may increase the hypertensive activities of Harmaline.	Withdrawn
Iproniazid	Iproniazid may increase the hypertensive activities of Harmaline.	Withdrawn
Irbesartan	Harmaline may increase the hypotensive activities of Irbesartan.	Approved, Investigational
Isocarboxazid	Isocarboxazid may increase the hypertensive activities of Harmaline.	Approved
Isoetarine	The risk or severity of adverse effects can be increased when Harmaline is combined with Isoetarine.	Approved
Isometheptene	The risk or severity of adverse effects can be increased when Harmaline is combined with Isometheptene.	Approved
Isoprenaline	The risk or severity of adverse effects can be increased when Harmaline is combined with Isoprenaline.	Approved, Investigational
Isosorbide Dinitrate	Harmaline may increase the orthostatic hypotensive activities of Isosorbide Dinitrate.	Approved, Investigational
Isradipine	Harmaline may increase the hypotensive activities of Isradipine.	Approved, Investigational
Ketanserin	Harmaline may increase the hypotensive activities of Ketanserin.	Investigational
Ketobemidone	The risk or severity of adverse effects can be increased when Ketobemidone is combined with Harmaline.	Approved, Investigational
L-Tryptophan	The risk or severity of adverse effects can be increased when L-Tryptophan is combined with Harmaline.	Approved, Nutraceutical, Withdrawn
Labetalol	Harmaline may increase the hypotensive activities of Labetalol.	Approved
Lacidipine	Harmaline may increase the hypotensive activities of Lacidipine.	Approved, Investigational
Lamotrigine	The risk or severity of adverse effects can be increased when Lamotrigine is combined with Harmaline.	Approved, Investigational
Latanoprost	Harmaline may increase the hypotensive activities of Latanoprost.	Approved, Investigational
Lercanidipine	Harmaline may increase the hypotensive activities of Lercanidipine.	Approved, Investigational
Levetiracetam	The risk or severity of adverse effects can be increased when Levetiracetam is combined with Harmaline.	Approved, Investigational
Levodopa	Harmaline may increase the orthostatic hypotensive activities of Levodopa.	Approved
Levomethadyl Acetate	The risk or severity of adverse effects can be increased when Levomethadyl Acetate is combined with Harmaline.	Approved, Investigational
Levomilnacipran	The risk or severity of adverse effects can be increased when Levomilnacipran is combined with Harmaline.	Approved, Investigational
Levonordefrin	Harmaline may increase the hypertensive activities of Levonordefrin.	Approved
Levorphanol	The risk or severity of adverse effects can be increased when Levorphanol is combined with Harmaline.	Approved
Levosalbutamol	The risk or severity of adverse effects can be increased when Harmaline is combined with Levosalbutamol.	Approved, Investigational
Linezolid	The risk or severity of adverse effects can be increased when Harmaline is combined with Linezolid.	Approved, Investigational
Linsidomine	Harmaline may increase the hypotensive activities of Linsidomine.	Experimental
Liraglutide	Harmaline may increase the hypoglycemic activities of Liraglutide.	Approved
Lisdexamfetamine	The risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with Harmaline.	Approved, Investigational
Lisinopril	Harmaline may increase the hypotensive activities of Lisinopril.	Approved, Investigational
Lisuride	The metabolism of Lisuride can be decreased when combined with Harmaline.	Approved, Investigational
Lithium cation	The risk or severity of adverse effects can be increased when Harmaline is combined with Lithium.	Experimental
Lofentanil	The risk or severity of adverse effects can be increased when Lofentanil is combined with Harmaline.	Illicit
Lofepramine	Harmaline may increase the serotonergic activities of Lofepramine.	Experimental
Lofexidine	The metabolism of Lofexidine can be decreased when combined with Harmaline.	Approved, Investigational
Loratadine	The risk or severity of adverse effects can be increased when Loratadine is combined with Harmaline.	Approved, Investigational
Lorpiprazole	The risk or severity of serotonin syndrome can be increased when Lorpiprazole is combined with Harmaline.	Approved
Losartan	Harmaline may increase the hypotensive activities of Losartan.	Approved
Macitentan	Harmaline may increase the hypotensive activities of Macitentan.	Approved
Magnesium carbonate	The risk or severity of adverse effects can be increased when Harmaline is combined with Magnesium carbonate.	Approved, Investigational
Magnesium citrate	The risk or severity of adverse effects can be increased when Harmaline is combined with Magnesium citrate.	Approved
Magnesium hydroxide	The risk or severity of adverse effects can be increased when Harmaline is combined with Magnesium hydroxide.	Approved, Investigational
Magnesium sulfate	The therapeutic efficacy of Harmaline can be increased when used in combination with Magnesium sulfate.	Approved, Investigational, Vet Approved
Magnesium Trisilicate	The risk or severity of adverse effects can be increased when Harmaline is combined with Magnesium Trisilicate.	Approved
Manidipine	Harmaline may increase the hypotensive activities of Manidipine.	Approved, Investigational
Maprotiline	The risk or severity of adverse effects can be increased when Harmaline is combined with Maprotiline.	Approved, Investigational
Mebanazine	Mebanazine may increase the hypertensive activities of Harmaline.	Withdrawn
Mecamylamine	Harmaline may increase the hypotensive activities of Mecamylamine.	Approved, Investigational
Mecasermin	Harmaline may increase the hypoglycemic activities of Mecasermin.	Approved, Investigational
Meclizine	The risk or severity of adverse effects can be increased when Meclizine is combined with Harmaline.	Approved
Melitracen	Harmaline may increase the serotonergic activities of Melitracen.	Experimental, Investigational
Mephedrone	The risk or severity of adverse effects can be increased when Mephedrone is combined with Harmaline.	Investigational
Mephentermine	The risk or severity of adverse effects can be increased when Mephentermine is combined with Harmaline.	Approved
Meptazinol	The risk or severity of adverse effects can be increased when Meptazinol is combined with Harmaline.	Experimental
Mequitazine	Harmaline may increase the anticholinergic activities of Mequitazine.	Approved
Metaraminol	Harmaline may increase the hypertensive activities of Metaraminol.	Approved, Investigational
Metformin	Harmaline may increase the hypoglycemic activities of Metformin.	Approved
Methadone	The risk or severity of adverse effects can be increased when Harmaline is combined with Methadone.	Approved
Methadyl Acetate	The risk or severity of adverse effects can be increased when Methadyl Acetate is combined with Harmaline.	Approved, Illicit
Methamphetamine	The risk or severity of adverse effects can be increased when Methamphetamine is combined with Harmaline.	Approved, Illicit
Methoserpidine	Harmaline may increase the hypotensive activities of Methoserpidine.	Experimental
Methoxamine	Harmaline may increase the hypertensive activities of Methoxamine.	Approved, Investigational
Methoxyphenamine	The risk or severity of adverse effects can be increased when Methoxyphenamine is combined with Harmaline.	Experimental
Methsuximide	The risk or severity of adverse effects can be increased when Methsuximide is combined with Harmaline.	Approved
Methyldopa	The risk or severity of hypertension can be increased when Harmaline is combined with Methyldopa.	Approved
Methylecgonine	The risk or severity of adverse effects can be increased when Methylecgonine is combined with Harmaline.	Experimental
Methylene blue	Harmaline may increase the serotonergic activities of Methylene blue.	Approved, Investigational
Methylphenidate	Harmaline may increase the hypertensive activities of Methylphenidate.	Approved, Investigational
Methysergide	The metabolism of Methysergide can be decreased when combined with Harmaline.	Approved
Metipranolol	Harmaline may increase the hypotensive activities of Metipranolol.	Approved
Metoclopramide	The risk or severity of serotonin syndrome can be increased when Metoclopramide is combined with Harmaline.	Approved, Investigational
Metolazone	Harmaline may increase the hypotensive activities of Metolazone.	Approved
Metoprolol	Harmaline may increase the hypotensive activities of Metoprolol.	Approved, Investigational
Metyrosine	Harmaline may increase the hypotensive activities of Metyrosine.	Approved
Mianserin	The risk or severity of adverse effects can be increased when Harmaline is combined with Mianserin.	Approved, Investigational
Mibefradil	Harmaline may increase the hypotensive activities of Mibefradil.	Investigational, Withdrawn
Midodrine	Harmaline may increase the hypertensive activities of Midodrine.	Approved
Midomafetamine	The risk or severity of adverse effects can be increased when Midomafetamine is combined with Harmaline.	Experimental, Illicit, Investigational
Mifepristone	Harmaline may increase the hypoglycemic activities of Mifepristone.	Approved, Investigational
Miglitol	Harmaline may increase the hypoglycemic activities of Miglitol.	Approved
Milnacipran	The risk or severity of adverse effects can be increased when Milnacipran is combined with Harmaline.	Approved, Investigational
Minaprine	Minaprine may increase the hypertensive activities of Harmaline.	Approved
Minoxidil	Harmaline may increase the hypotensive activities of Minoxidil.	Approved, Investigational
Mirtazapine	The risk or severity of adverse effects can be increased when Harmaline is combined with Mirtazapine.	Approved
MMDA	The risk or severity of adverse effects can be increased when MMDA is combined with Harmaline.	Experimental, Illicit
Moclobemide	The risk or severity of adverse effects can be increased when Harmaline is combined with Moclobemide.	Approved, Investigational
Morphine	The therapeutic efficacy of Morphine can be increased when used in combination with Harmaline.	Approved, Investigational
Moxonidine	Harmaline may increase the hypotensive activities of Moxonidine.	Approved, Investigational
Muzolimine	Harmaline may increase the hypotensive activities of Muzolimine.	Experimental
Nadolol	Harmaline may increase the hypotensive activities of Nadolol.	Approved
Naftopidil	Harmaline may increase the hypotensive activities of Naftopidil.	Investigational
Nalbuphine	The risk or severity of adverse effects can be increased when Nalbuphine is combined with Harmaline.	Approved
Naluzotan	The metabolism of Naluzotan can be decreased when combined with Harmaline.	Investigational
Naphazoline	Harmaline may increase the hypertensive activities of Naphazoline.	Approved
Naratriptan	The serum concentration of Naratriptan can be increased when it is combined with Harmaline.	Approved, Investigational
Nateglinide	Harmaline may increase the hypoglycemic activities of Nateglinide.	Approved, Investigational
Nebivolol	Harmaline may increase the hypotensive activities of Nebivolol.	Approved, Investigational
Nefazodone	The risk or severity of adverse effects can be increased when Nefazodone is combined with Harmaline.	Approved, Withdrawn
Neomycin	The risk or severity of adverse effects can be increased when Harmaline is combined with Neomycin.	Approved, Vet Approved
Nialamide	Nialamide may increase the hypertensive activities of Harmaline.	Withdrawn
Nicardipine	Harmaline may increase the hypotensive activities of Nicardipine.	Approved, Investigational
Nicorandil	Harmaline may increase the hypotensive activities of Nicorandil.	Approved, Investigational
Nifedipine	Harmaline may increase the orthostatic hypotensive activities of Nifedipine.	Approved
Niguldipine	Harmaline may increase the hypotensive activities of Niguldipine.	Experimental
Nilvadipine	Harmaline may increase the hypotensive activities of Nilvadipine.	Approved, Investigational
Nimodipine	Harmaline may increase the hypotensive activities of Nimodipine.	Approved, Investigational
Nisoldipine	Harmaline may increase the hypotensive activities of Nisoldipine.	Approved
Nitrendipine	Harmaline may increase the hypotensive activities of Nitrendipine.	Approved, Investigational
Nitroprusside	Harmaline may increase the hypotensive activities of Nitroprusside.	Approved, Investigational
Norepinephrine	Harmaline may increase the hypertensive activities of Norepinephrine.	Approved
Normethadone	The risk or severity of adverse effects can be increased when Normethadone is combined with Harmaline.	Approved, Illicit
Nortriptyline	Harmaline may increase the serotonergic activities of Nortriptyline.	Approved
Octamoxin	Octamoxin may increase the hypertensive activities of Harmaline.	Withdrawn
Olanzapine	Harmaline may increase the serotonergic activities of Olanzapine.	Approved, Investigational
Olmesartan	Harmaline may increase the hypotensive activities of Olmesartan.	Approved, Investigational
Olodaterol	The risk or severity of adverse effects can be increased when Harmaline is combined with Olodaterol.	Approved
Omapatrilat	Harmaline may increase the hypotensive activities of Omapatrilat.	Investigational
Ondansetron	The risk or severity of serotonin syndrome can be increased when Ondansetron is combined with Harmaline.	Approved
Opipramol	Harmaline may increase the serotonergic activities of Opipramol.	Investigational
Opium	The risk or severity of adverse effects can be increased when Opium is combined with Harmaline.	Approved, Illicit
Orciprenaline	The risk or severity of adverse effects can be increased when Harmaline is combined with Orciprenaline.	Approved
Oxycodone	Harmaline may increase the serotonergic and central nervous system depressant (CNS depressant) activities of Oxycodone.	Approved, Illicit, Investigational
Oxymetazoline	Harmaline may increase the hypertensive activities of Oxymetazoline.	Approved, Investigational
Oxymorphone	The risk or severity of adverse effects can be increased when Oxymorphone is combined with Harmaline.	Approved, Investigational, Vet Approved
Pargyline	Pargyline may increase the hypertensive activities of Harmaline.	Approved
Paromomycin	The risk or severity of adverse effects can be increased when Harmaline is combined with Paromomycin.	Approved, Investigational
Paroxetine	Harmaline may increase the serotonergic activities of Paroxetine.	Approved, Investigational
Penbutolol	Harmaline may increase the hypotensive activities of Penbutolol.	Approved, Investigational
Penfluridol	The risk or severity of adverse effects can be increased when Penfluridol is combined with Harmaline.	Experimental
Pentamidine	Harmaline may increase the hypoglycemic activities of Pentamidine.	Approved, Investigational
Pentazocine	The risk or severity of adverse effects can be increased when Pentazocine is combined with Harmaline.	Approved, Vet Approved
Pentolinium	Harmaline may increase the hypotensive activities of Pentolinium.	Approved
Pergolide	The metabolism of Pergolide can be decreased when combined with Harmaline.	Approved, Investigational, Vet Approved, Withdrawn
Perindopril	Harmaline may increase the hypotensive activities of Perindopril.	Approved
Pethidine	Harmaline may increase the hypotensive and central nervous system depressant (CNS depressant) activities of Pethidine.	Approved
PF-00610355	The risk or severity of adverse effects can be increased when Harmaline is combined with PF-00610355.	Investigational
Phenazocine	The risk or severity of adverse effects can be increased when Phenazocine is combined with Harmaline.	Experimental
Phendimetrazine	Harmaline may increase the hypertensive activities of Phendimetrazine.	Approved, Illicit
Phenelzine	Phenelzine may increase the hypertensive activities of Harmaline.	Approved
Pheniprazine	Pheniprazine may increase the hypertensive activities of Harmaline.	Withdrawn
Phenobarbital	The risk or severity of adverse effects can be increased when Phenobarbital is combined with Harmaline.	Approved, Investigational
Phenoperidine	The risk or severity of adverse effects can be increased when Phenoperidine is combined with Harmaline.	Experimental
Phenoxybenzamine	Harmaline may increase the hypotensive activities of Phenoxybenzamine.	Approved
Phenoxypropazine	Phenoxypropazine may increase the hypertensive activities of Harmaline.	Withdrawn
Phentermine	The risk or severity of adverse effects can be increased when Phentermine is combined with Harmaline.	Approved, Illicit
Phenylephrine	Harmaline may increase the hypertensive activities of Phenylephrine.	Approved
Phenylpropanolamine	The risk or severity of adverse effects can be increased when Harmaline is combined with Phenylpropanolamine.	Approved, Vet Approved, Withdrawn
Pholcodine	Pholcodine may increase the serotonergic activities of Harmaline.	Approved, Illicit
Piclozotan	The metabolism of Piclozotan can be decreased when combined with Harmaline.	Investigational
Pinacidil	Harmaline may increase the hypotensive activities of Pinacidil.	Approved
Pindolol	Harmaline may increase the hypotensive activities of Pindolol.	Approved, Investigational
Pioglitazone	Harmaline may increase the hypoglycemic activities of Pioglitazone.	Approved, Investigational
Pirbuterol	The risk or severity of adverse effects can be increased when Harmaline is combined with Pirbuterol.	Approved
Piritramide	The risk or severity of adverse effects can be increased when Piritramide is combined with Harmaline.	Approved, Investigational
Pirlindole	Pirlindole may increase the hypertensive activities of Harmaline.	Approved
Pivhydrazine	Pivhydrazine may increase the hypertensive activities of Harmaline.	Withdrawn
Pizotifen	Harmaline may increase the anticholinergic activities of Pizotifen.	Approved
Platelet Activating Factor	Harmaline may increase the hypotensive activities of Platelet Activating Factor.	Experimental
Polymyxin B Sulfate	The risk or severity of adverse effects can be increased when Harmaline is combined with Polymyxin B Sulfate.	Approved, Vet Approved
Polythiazide	Harmaline may increase the hypotensive activities of Polythiazide.	Approved
Pramipexole	Harmaline may increase the sedative activities of Pramipexole.	Approved, Investigational
Pramlintide	Harmaline may increase the hypoglycemic activities of Pramlintide.	Approved, Investigational
Prazosin	Harmaline may increase the hypotensive activities of Prazosin.	Approved
Pregabalin	The therapeutic efficacy of Harmaline can be increased when used in combination with Pregabalin.	Approved, Illicit, Investigational
Procaine	Harmaline may increase the hypertensive activities of Procaine.	Approved, Investigational, Vet Approved
Procarbazine	Harmaline may increase the hypertensive activities of Procarbazine.	Approved, Investigational
Procaterol	The risk or severity of adverse effects can be increased when Harmaline is combined with Procaterol.	Approved, Investigational
Prochlorperazine	The risk or severity of adverse effects can be increased when Prochlorperazine is combined with Harmaline.	Approved, Vet Approved
Promethazine	The risk or severity of adverse effects can be increased when Promethazine is combined with Harmaline.	Approved, Investigational
Propranolol	Harmaline may increase the hypotensive activities of Propranolol.	Approved, Investigational
Protokylol	The risk or severity of adverse effects can be increased when Harmaline is combined with Protokylol.	Approved, Vet Approved
Protriptyline	Harmaline may increase the serotonergic activities of Protriptyline.	Approved
Pseudoephedrine	Harmaline may increase the hypertensive activities of Pseudoephedrine.	Approved
Pyrantel	The risk or severity of adverse effects can be increased when Harmaline is combined with Pyrantel.	Approved, Vet Approved
Quetiapine	Harmaline may increase the orthostatic hypotensive activities of Quetiapine.	Approved
Quinapril	Harmaline may increase the hypotensive activities of Quinapril.	Approved, Investigational
Quinine	Harmaline may increase the hypoglycemic activities of Quinine.	Approved
Racepinephrine	Harmaline may increase the hypertensive activities of Racepinephrine.	Approved
Ramipril	Harmaline may increase the hypotensive activities of Ramipril.	Approved
Rasagiline	Rasagiline may increase the hypertensive activities of Harmaline.	Approved
Remifentanil	The risk or severity of adverse effects can be increased when Remifentanil is combined with Harmaline.	Approved
Remikiren	Harmaline may increase the hypotensive activities of Remikiren.	Approved
Repaglinide	Harmaline may increase the hypoglycemic activities of Repaglinide.	Approved, Investigational
Rescinnamine	Harmaline may increase the hypotensive activities of Rescinnamine.	Approved
Reserpine	The risk or severity of adverse effects can be increased when Harmaline is combined with Reserpine.	Approved, Investigational
Rilmenidine	Harmaline may increase the hypotensive activities of Rilmenidine.	Approved, Investigational
Riociguat	Harmaline may increase the hypotensive activities of Riociguat.	Approved
Ritobegron	The risk or severity of adverse effects can be increased when Ritobegron is combined with Harmaline.	Investigational
Ritodrine	The risk or severity of adverse effects can be increased when Harmaline is combined with Ritodrine.	Approved, Investigational
Rizatriptan	The metabolism of Rizatriptan can be decreased when combined with Harmaline.	Approved
Ropinirole	Harmaline may increase the sedative activities of Ropinirole.	Approved, Investigational
Rosiglitazone	Harmaline may increase the hypoglycemic activities of Rosiglitazone.	Approved, Investigational
Rotigotine	The metabolism of Rotigotine can be decreased when combined with Harmaline.	Approved
Safrazine	Safrazine may increase the hypertensive activities of Harmaline.	Withdrawn
Salbutamol	The risk or severity of adverse effects can be increased when Harmaline is combined with Salbutamol.	Approved, Vet Approved
Salmeterol	The risk or severity of adverse effects can be increased when Harmaline is combined with Salmeterol.	Approved
Saprisartan	Harmaline may increase the hypotensive activities of Saprisartan.	Experimental
Saxagliptin	Harmaline may increase the hypoglycemic activities of Saxagliptin.	Approved
Scopolamine	The risk or severity of adverse effects can be increased when Scopolamine is combined with Harmaline.	Approved, Investigational
Selegiline	Selegiline may increase the hypertensive activities of Harmaline.	Approved, Investigational, Vet Approved
Selexipag	Harmaline may increase the hypotensive activities of Selexipag.	Approved
Sertraline	The risk or severity of adverse effects can be increased when Sertraline is combined with Harmaline.	Approved
Sitagliptin	Harmaline may increase the hypoglycemic activities of Sitagliptin.	Approved, Investigational
Sitaxentan	Harmaline may increase the hypotensive activities of Sitaxentan.	Approved, Investigational, Withdrawn
Spirapril	Harmaline may increase the hypotensive activities of Spirapril.	Approved
Spironolactone	Harmaline may increase the orthostatic hypotensive activities of Spironolactone.	Approved
Sufentanil	The risk or severity of adverse effects can be increased when Sufentanil is combined with Harmaline.	Approved, Investigational
Sulfadiazine	Harmaline may increase the hypoglycemic activities of Sulfadiazine.	Approved, Investigational, Vet Approved
Sulfamethoxazole	Harmaline may increase the hypoglycemic activities of Sulfamethoxazole.	Approved
Sulfisoxazole	Harmaline may increase the hypoglycemic activities of Sulfisoxazole.	Approved, Vet Approved
Sumatriptan	The metabolism of Sumatriptan can be decreased when combined with Harmaline.	Approved, Investigational
Sunitinib	Harmaline may increase the hypoglycemic activities of Sunitinib.	Approved, Investigational
Talinolol	Harmaline may increase the hypotensive activities of Talinolol.	Investigational
Tapentadol	The risk or severity of adverse effects can be increased when Tapentadol is combined with Harmaline.	Approved
Telmisartan	Harmaline may increase the hypotensive activities of Telmisartan.	Approved, Investigational
Temocapril	Harmaline may increase the hypotensive activities of Temocapril.	Experimental, Investigational
Terbutaline	The risk or severity of adverse effects can be increased when Harmaline is combined with Terbutaline.	Approved
Terlipressin	Harmaline may increase the hypotensive activities of Terlipressin.	Approved, Investigational
Tetrabenazine	The risk or severity of adverse effects can be increased when Harmaline is combined with Tetrabenazine.	Approved, Investigational
Tetracycline	The risk or severity of adverse effects can be increased when Harmaline is combined with Tetracycline.	Approved, Vet Approved
Tetrahydrocannabivarin	The metabolism of Tetrahydrocannabivarin can be decreased when combined with Harmaline.	Investigational
Tetrahydropalmatine	Harmaline may increase the hypotensive activities of Tetrahydropalmatine.	Investigational
Tetryzoline	Harmaline may increase the hypertensive activities of Tetryzoline.	Approved
Theodrenaline	Harmaline may increase the hypotensive activities of Theodrenaline.	Investigational
Tianeptine	The risk or severity of adverse effects can be increased when Tianeptine is combined with Harmaline.	Approved, Investigational
Tibolone	Harmaline may increase the hypotensive activities of Tibolone.	Approved, Investigational
Ticrynafen	Harmaline may increase the hypotensive activities of Ticrynafen.	Withdrawn
Tilidine	The risk or severity of adverse effects can be increased when Tilidine is combined with Harmaline.	Experimental
Timolol	Harmaline may increase the hypotensive activities of Timolol.	Approved
Tolazamide	Harmaline may increase the hypoglycemic activities of Tolazamide.	Approved, Investigational
Tolazoline	Harmaline may increase the hypotensive activities of Tolazoline.	Approved, Vet Approved
Tolbutamide	Harmaline may increase the hypoglycemic activities of Tolbutamide.	Approved, Investigational
Tolcapone	The risk or severity of adverse effects can be increased when Tolcapone is combined with Harmaline.	Approved, Withdrawn
Tolonidine	Harmaline may increase the hypotensive activities of Tolonidine.	Experimental
Toloxatone	Toloxatone may increase the hypertensive activities of Harmaline.	Approved
Topiramate	The risk or severity of adverse effects can be increased when Topiramate is combined with Harmaline.	Approved
Torasemide	Harmaline may increase the hypotensive activities of Torasemide.	Approved
Tramadol	The risk or severity of serotonin syndrome and seizure can be increased when Harmaline is combined with Tramadol.	Approved, Investigational
Trandolapril	Harmaline may increase the hypotensive activities of Trandolapril.	Approved
Tranylcypromine	Tranylcypromine may increase the hypertensive activities of Harmaline.	Approved, Investigational
Travoprost	Harmaline may increase the hypotensive activities of Travoprost.	Approved
Trazodone	Harmaline may increase the serotonergic activities of Trazodone.	Approved, Investigational
Treprostinil	Harmaline may increase the hypotensive activities of Treprostinil.	Approved, Investigational
Trichlormethiazide	Harmaline may increase the hypotensive activities of Trichlormethiazide.	Approved, Vet Approved
Trimazosin	Harmaline may increase the hypotensive activities of Trimazosin.	Experimental
Trimethadione	The risk or severity of adverse effects can be increased when Harmaline is combined with Trimethadione.	Approved
Trimethaphan	Harmaline may increase the hypotensive activities of Trimethaphan.	Approved, Investigational
Trimipramine	Harmaline may increase the serotonergic activities of Trimipramine.	Approved
Unoprostone	Harmaline may increase the hypotensive activities of Unoprostone.	Approved, Investigational
Urapidil	Harmaline may increase the hypotensive activities of Urapidil.	Investigational
Valproic Acid	The risk or severity of adverse effects can be increased when Valproic Acid is combined with Harmaline.	Approved, Investigational
Valsartan	Harmaline may increase the hypotensive activities of Valsartan.	Approved, Investigational
Vancomycin	The risk or severity of adverse effects can be increased when Harmaline is combined with Vancomycin.	Approved
Vecuronium	The risk or severity of adverse effects can be increased when Harmaline is combined with Vecuronium.	Approved
Venlafaxine	Harmaline may increase the serotonergic activities of Venlafaxine.	Approved
Verapamil	Harmaline may increase the orthostatic hypotensive activities of Verapamil.	Approved
Vilanterol	The risk or severity of adverse effects can be increased when Harmaline is combined with Vilanterol.	Approved
Vilazodone	The metabolism of Vilazodone can be decreased when combined with Harmaline.	Approved
Vincamine	Harmaline may increase the hypotensive activities of Vincamine.	Experimental
Vinpocetine	The risk or severity of adverse effects can be increased when Harmaline is combined with Vinpocetine.	Investigational
Vortioxetine	The metabolism of Vortioxetine can be decreased when combined with Harmaline.	Approved, Investigational
Xipamide	Harmaline may increase the hypotensive activities of Xipamide.	Experimental
Xylometazoline	Harmaline may increase the hypertensive activities of Xylometazoline.	Approved, Investigational
Ziconotide	The risk or severity of adverse effects can be increased when Ziconotide is combined with Harmaline.	Approved
Zimelidine	The risk or severity of adverse effects can be increased when Zimelidine is combined with Harmaline.	Withdrawn
Ziprasidone	The metabolism of Ziprasidone can be decreased when combined with Harmaline.	Approved
Zofenopril	Harmaline may increase the hypotensive activities of Zofenopril.	Experimental
Zolmitriptan	The metabolism of Zolmitriptan can be decreased when combined with Harmaline.	Approved, Investigational
Zolpidem	Harmaline may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.	Approved
Zonisamide	The risk or severity of adverse effects can be increased when Zonisamide is combined with Harmaline.	Approved, Investigational

Food Interactions

Not Available

References

General References

Not Available

External Links

Human Metabolome Database: HMDB0030310
KEGG Compound: C06536
PubChem Compound: 5280951
PubChem Substance: 347829327
ChemSpider: 10211258
BindingDB: 50029799
ChEBI: 28172
ChEMBL: CHEMBL340807
Wikipedia: Harmaline

Clinical Trials

Clinical Trials: Not Available

Pharmacoeconomics

Manufacturers: Not Available
Packagers: Not Available
Dosage forms: Not Available
Prices: Not Available
Patents: Not Available

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0576 mg/mL	ALOGPS
logP	2.61	ALOGPS
logP	1.67	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	14.95	ChemAxon
pKa (Strongest Basic)	6.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	64.15 m³·mol^-1	ChemAxon
Polarizability	24.2 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
MS/MS Spectrum - , positive	LC-MS/MS	splash10-00di-2920000000-44473ef3fbb78c164b21

Taxonomy

Description: This compound belongs to the class of organic compounds known as harmala alkaloids. These are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.
Kingdom: Organic compounds
Super Class: Alkaloids and derivatives
Class: Harmala alkaloids
Sub Class: Not Available
Direct Parent: Harmala alkaloids
Alternative Parents: Beta carbolines / 3-alkylindoles / Anisoles / Alkyl aryl ethers / Pyrroles / Heteroaromatic compounds / Ketimines / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Organopnictogen compoundsHydrocarbon derivatives
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Substituents: Harmaline / Harman / Beta-carboline / Pyridoindole / 3-alkylindole / Indole or derivatives / Indole / Anisole / Alkyl aryl ether / Benzenoid
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Molecular Framework: Aromatic heteropolycyclic compounds
External Descriptors: harmala alkaloid (CHEBI:28172) / Indole alkaloids (C06536) / an alkaloid (CPD-9939)

Targets

Details1. Histamine N-methyltransferase

Kind: Protein
Organism: Human
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Histamine n-methyltransferase activity
Specific Function: Inactivates histamine by N-methylation. Plays an important role in degrading histamine and in regulating the airway response to histamine.
Gene Name: HNMT
Uniprot ID: P50135
Uniprot Name: Histamine N-methyltransferase
Molecular Weight: 33294.765 Da

References

Cumming P, Vincent SR: Inhibition of histamine-N-methyltransferase (HNMT) by fragments of 9-amino-1,2,3,4-tetrahydroacridine (tacrine) and by beta-carbolines. Biochem Pharmacol. 1992 Sep 1;44(5):989-92. [PubMed:1530666]

Drug created on August 02, 2017 13:23 / Updated on August 15, 2018 10:02

Harmaline

Identification

Structure for DB13875 (Harmaline)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References