This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Harmaline
Accession Number
DB13875
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Harmaline hydrochloride64056X913V363-11-1PULNGKOFHCQQQA-UHFFFAOYSA-N
Harmaline hydrochloride dihydrate5B4DGH2M9R6027-98-1LCEKUHFBUFUSSY-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
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UHistamine N-methyltransferase
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
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
DrugInteractionDrug group
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with Harmaline.Experimental, Illicit
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Harmaline.Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Harmaline.Experimental, Illicit
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypertensive activities of Harmaline.Experimental
AcarboseHarmaline may increase the hypoglycemic activities of Acarbose.Approved, Investigational
AcebutololHarmaline may increase the hypotensive activities of Acebutolol.Approved
AlaproclateThe risk or severity of adverse effects can be increased when Alaproclate is combined with Harmaline.Experimental
AlbiglutideHarmaline may increase the hypoglycemic activities of Albiglutide.Approved
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Harmaline.Approved, Illicit
AliskirenHarmaline may increase the hypotensive activities of Aliskiren.Approved, Investigational
AlmotriptanThe serum concentration of Almotriptan can be increased when it is combined with Harmaline.Approved, Investigational
AlogliptinHarmaline may increase the hypoglycemic activities of Alogliptin.Approved
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Alphacetylmethadol is combined with Harmaline.Experimental, Illicit
AlphaprodineThe risk or severity of adverse effects can be increased when Alphaprodine is combined with Harmaline.Illicit
AlprenololHarmaline may increase the hypotensive activities of Alprenolol.Approved, Withdrawn
AltretamineAltretamine may increase the orthostatic hypotensive activities of Harmaline.Approved
AmbrisentanHarmaline may increase the hypotensive activities of Ambrisentan.Approved, Investigational
AmineptineHarmaline may increase the serotonergic activities of Amineptine.Illicit, Withdrawn
AmitriptylineHarmaline may increase the serotonergic activities of Amitriptyline.Approved
AmlodipineHarmaline may increase the hypotensive activities of Amlodipine.Approved
AmoxapineThe risk or severity of adverse effects can be increased when Harmaline is combined with Amoxapine.Approved
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Harmaline.Approved, Illicit
ApomorphineThe metabolism of Apomorphine can be decreased when combined with Harmaline.Approved, Investigational
ApraclonidineThe risk or severity of adverse effects can be increased when Harmaline is combined with Apraclonidine.Approved
ArbutamineThe risk or severity of adverse effects can be increased when Harmaline is combined with Arbutamine.Approved
ArformoterolThe risk or severity of adverse effects can be increased when Harmaline is combined with Arformoterol.Approved, Investigational
AtenololHarmaline may increase the hypotensive activities of Atenolol.Approved
AtomoxetineHarmaline may increase the central neurotoxic activities of Atomoxetine.Approved
AtropineHarmaline may increase the hypertensive activities of Atropine.Approved, Vet Approved
BambuterolThe risk or severity of adverse effects can be increased when Harmaline is combined with Bambuterol.Approved, Investigational
BenazeprilHarmaline may increase the hypotensive activities of Benazepril.Approved, Investigational
BendroflumethiazideHarmaline may increase the hypotensive activities of Bendroflumethiazide.Approved
BenmoxinHarmaline may increase the hypertensive activities of Benmoxin.Withdrawn
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Harmaline.Approved, Illicit
BepridilHarmaline may increase the hypotensive activities of Bepridil.Approved, Withdrawn
BetahistineThe serum concentration of Betahistine can be increased when it is combined with Harmaline.Approved
BetaxololHarmaline may increase the hypotensive activities of Betaxolol.Approved
BethanidineHarmaline may increase the hypotensive activities of Bethanidine.Approved
BezafibrateThe risk or severity of adverse effects can be increased when Harmaline is combined with Bezafibrate.Approved
BietaserpineHarmaline may increase the hypotensive activities of Bietaserpine.Experimental
BimatoprostHarmaline may increase the hypotensive activities of Bimatoprost.Approved, Investigational
BisoprololHarmaline may increase the hypotensive activities of Bisoprolol.Approved
BosentanHarmaline may increase the hypotensive activities of Bosentan.Approved, Investigational
BQ-123Harmaline may increase the hypotensive activities of BQ-123.Investigational
BretyliumHarmaline may increase the hypotensive activities of Bretylium.Approved
BrimonidineThe risk or severity of adverse effects can be increased when Harmaline is combined with Brimonidine.Approved
BrofaromineHarmaline may increase the hypertensive activities of Brofaromine.Experimental
BromocriptineHarmaline may increase the hypoglycemic activities of Bromocriptine.Approved, Investigational
BupranololHarmaline may increase the hypotensive activities of Bupranolol.Approved
BuprenorphineThe risk or severity of adverse effects can be increased when Buprenorphine is combined with Harmaline.Approved, Illicit, Investigational, Vet Approved
BupropionHarmaline may increase the hypertensive activities of Bupropion.Approved
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Harmaline.Approved, Investigational
ButorphanolThe risk or severity of adverse effects can be increased when Butorphanol is combined with Harmaline.Approved, Illicit, Vet Approved
CabergolineThe metabolism of Cabergoline can be decreased when combined with Harmaline.Approved
CadralazineHarmaline may increase the hypotensive activities of Cadralazine.Experimental
CafedrineHarmaline may increase the hypotensive activities of Cafedrine.Investigational
CanagliflozinHarmaline may increase the hypoglycemic activities of Canagliflozin.Approved
CandesartanHarmaline may increase the hypotensive activities of Candesartan.Experimental
Candesartan cilexetilHarmaline may increase the hypotensive activities of Candesartan cilexetil.Approved
CandoxatrilHarmaline may increase the hypotensive activities of Candoxatril.Experimental
CaptoprilHarmaline may increase the hypotensive activities of Captopril.Approved
CarbamazepineThe risk or severity of adverse effects can be increased when Carbamazepine is combined with Harmaline.Approved, Investigational
CarfentanilThe risk or severity of adverse effects can be increased when Carfentanil is combined with Harmaline.Illicit, Investigational, Vet Approved
CaroxazoneHarmaline may increase the hypertensive activities of Caroxazone.Withdrawn
CarteololHarmaline may increase the hypotensive activities of Carteolol.Approved
CarvedilolHarmaline may increase the hypotensive activities of Carvedilol.Approved, Investigational
CeliprololHarmaline may increase the hypotensive activities of Celiprolol.Approved, Investigational
ChlorothiazideHarmaline may increase the hypotensive activities of Chlorothiazide.Approved, Vet Approved
ChlorphentermineThe risk or severity of adverse effects can be increased when Chlorphentermine is combined with Harmaline.Illicit, Withdrawn
ChlorpropamideHarmaline may increase the hypoglycemic activities of Chlorpropamide.Approved
ChlorthalidoneHarmaline may increase the hypotensive activities of Chlorthalidone.Approved
CicletanineHarmaline may increase the hypotensive activities of Cicletanine.Investigational
CilazaprilHarmaline may increase the hypotensive activities of Cilazapril.Approved
CirazolineHarmaline may increase the hypertensive activities of Cirazoline.Experimental
CitalopramThe risk or severity of adverse effects can be increased when Citalopram is combined with Harmaline.Approved
ClemastineHarmaline may increase the anticholinergic activities of Clemastine.Approved
ClenbuterolThe risk or severity of adverse effects can be increased when Harmaline is combined with Clenbuterol.Approved, Investigational, Vet Approved
ClomipramineHarmaline may increase the serotonergic activities of Clomipramine.Approved, Vet Approved
ClonidineHarmaline may increase the hypotensive activities of Clonidine.Approved
CloranololHarmaline may increase the hypotensive activities of Cloranolol.Experimental
CodeineThe risk or severity of adverse effects can be increased when Codeine is combined with Harmaline.Approved, Illicit
CryptenamineHarmaline may increase the hypotensive activities of Cryptenamine.Approved
CyclobenzaprineCyclobenzaprine may increase the serotonergic activities of Harmaline.Approved
CyclopenthiazideHarmaline may increase the hypotensive activities of Cyclopenthiazide.Experimental
CyclothiazideHarmaline may increase the hypotensive activities of Cyclothiazide.Approved
CyproheptadineHarmaline may increase the anticholinergic activities of Cyproheptadine.Approved
DapagliflozinHarmaline may increase the hypoglycemic activities of Dapagliflozin.Approved
DapoxetineThe risk or severity of adverse effects can be increased when Dapoxetine is combined with Harmaline.Investigational
DebrisoquinHarmaline may increase the hypotensive activities of Debrisoquin.Approved, Investigational
DelaprilHarmaline may increase the hypotensive activities of Delapril.Experimental
DeserpidineHarmaline may increase the hypotensive activities of Deserpidine.Approved
DesipramineHarmaline may increase the serotonergic activities of Desipramine.Approved
DesvenlafaxineThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with Harmaline.Approved
DexmethylphenidateHarmaline may increase the hypertensive activities of Dexmethylphenidate.Approved
DextroamphetamineThe risk or severity of adverse effects can be increased when Dextroamphetamine is combined with Harmaline.Approved, Illicit
DextromethorphanHarmaline may increase the serotonergic activities of Dextromethorphan.Approved
DextromoramideThe risk or severity of adverse effects can be increased when Dextromoramide is combined with Harmaline.Experimental, Illicit
DextropropoxypheneThe risk or severity of adverse effects can be increased when Dextropropoxyphene is combined with Harmaline.Approved, Illicit, Investigational, Withdrawn
DezocineThe risk or severity of adverse effects can be increased when Dezocine is combined with Harmaline.Approved, Investigational
DiazoxideHarmaline may increase the hypotensive activities of Diazoxide.Approved
DibenzepinHarmaline may increase the serotonergic activities of Dibenzepin.Experimental
diethylnorspermineHarmaline may increase the hypotensive activities of diethylnorspermine.Investigational
DiethylpropionHarmaline may increase the hypertensive activities of Diethylpropion.Approved, Illicit
DihydralazineHarmaline may increase the hypotensive activities of Dihydralazine.Investigational
DihydrocodeineThe risk or severity of adverse effects can be increased when Dihydrocodeine is combined with Harmaline.Approved, Illicit
DihydroergotamineThe metabolism of Dihydroergotamine can be decreased when combined with Harmaline.Approved
DihydroetorphineThe risk or severity of adverse effects can be increased when Dihydroetorphine is combined with Harmaline.Experimental, Illicit
DihydromorphineThe risk or severity of adverse effects can be increased when Dihydromorphine is combined with Harmaline.Experimental, Illicit
DiltiazemHarmaline may increase the hypotensive activities of Diltiazem.Approved
DiphenoxylateThe risk or severity of adverse effects can be increased when Diphenoxylate is combined with Harmaline.Approved, Illicit
DipivefrinThe risk or severity of adverse effects can be increased when Harmaline is combined with Dipivefrin.Approved
DisopyramideHarmaline may increase the hypoglycemic activities of Disopyramide.Approved
DobutamineThe risk or severity of adverse effects can be increased when Harmaline is combined with Dobutamine.Approved
DomperidoneThe risk or severity of adverse effects can be increased when Harmaline is combined with Domperidone.Approved, Investigational, Vet Approved
DorzolamideHarmaline may increase the hypotensive activities of Dorzolamide.Approved
DosulepinHarmaline may increase the serotonergic activities of Dosulepin.Approved
DoxapramHarmaline may increase the hypertensive activities of Doxapram.Approved, Vet Approved
DoxazosinHarmaline may increase the hypotensive activities of Doxazosin.Approved
DoxepinHarmaline may increase the serotonergic activities of Doxepin.Approved
DoxylamineHarmaline may increase the anticholinergic activities of Doxylamine.Approved, Vet Approved
DPDPEThe risk or severity of adverse effects can be increased when DPDPE is combined with Harmaline.Experimental
DrotebanolThe risk or severity of adverse effects can be increased when Drotebanol is combined with Harmaline.Experimental, Illicit
DroxidopaThe risk or severity of adverse effects can be increased when Harmaline is combined with Droxidopa.Approved, Investigational
DulaglutideHarmaline may increase the hypoglycemic activities of Dulaglutide.Approved
DuloxetineThe risk or severity of adverse effects can be increased when Duloxetine is combined with Harmaline.Approved
EcgonineThe risk or severity of adverse effects can be increased when Ecgonine is combined with Harmaline.Experimental, Illicit
EfonidipineHarmaline may increase the hypotensive activities of Efonidipine.Approved, Investigational
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Harmaline.Approved, Investigational
EmpagliflozinHarmaline may increase the hypoglycemic activities of Empagliflozin.Approved
EnalaprilHarmaline may increase the hypotensive activities of Enalapril.Approved, Vet Approved
EnalaprilatHarmaline may increase the hypotensive activities of Enalaprilat.Approved
EndralazineHarmaline may increase the hypotensive activities of Endralazine.Experimental
EntacaponeThe risk or severity of adverse effects can be increased when Entacapone is combined with Harmaline.Approved, Investigational
EpanololHarmaline may increase the hypotensive activities of Epanolol.Experimental
EphedraThe risk or severity of adverse effects can be increased when Harmaline is combined with Ephedra.Approved, Nutraceutical, Withdrawn
EpinephrineHarmaline may increase the hypertensive activities of Epinephrine.Approved, Vet Approved
EpoprostenolHarmaline may increase the hypotensive activities of Epoprostenol.Approved
EprosartanHarmaline may increase the hypotensive activities of Eprosartan.Approved
ErgotamineHarmaline may increase the hypertensive activities of Ergotamine.Approved
EscitalopramThe risk or severity of adverse effects can be increased when Escitalopram is combined with Harmaline.Approved, Investigational
EsmirtazapineHarmaline may increase the serotonergic activities of Esmirtazapine.Investigational
EthanolThe risk or severity of adverse effects can be increased when Ethanol is combined with Harmaline.Approved
EthylmorphineThe risk or severity of adverse effects can be increased when Ethylmorphine is combined with Harmaline.Approved, Illicit
EtoperidoneThe risk or severity of adverse effects can be increased when Etoperidone is combined with Harmaline.Withdrawn
EtorphineThe risk or severity of adverse effects can be increased when Etorphine is combined with Harmaline.Illicit, Vet Approved
ExenatideHarmaline may increase the hypoglycemic activities of Exenatide.Approved, Investigational
FelodipineHarmaline may increase the hypotensive activities of Felodipine.Approved, Investigational
FenfluramineThe risk or severity of adverse effects can be increased when Harmaline is combined with Fenfluramine.Illicit, Investigational, Withdrawn
FenoldopamHarmaline may increase the hypotensive activities of Fenoldopam.Approved
FenoterolThe risk or severity of adverse effects can be increased when Harmaline is combined with Fenoterol.Approved, Investigational
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Harmaline.Approved, Illicit, Investigational, Vet Approved
Ferulic acidHarmaline may increase the hypotensive activities of Ferulic acid.Experimental
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Harmaline.Approved, Vet Approved
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Harmaline.Approved, Investigational
FormoterolThe risk or severity of adverse effects can be increased when Harmaline is combined with Formoterol.Approved, Investigational
FosinoprilHarmaline may increase the hypotensive activities of Fosinopril.Approved
FrovatriptanThe serum concentration of Frovatriptan can be increased when it is combined with Harmaline.Approved, Investigational
FurazolidoneFurazolidone may increase the hypertensive activities of Harmaline.Approved, Investigational, Vet Approved
GepefrineThe risk or severity of adverse effects can be increased when Gepefrine is combined with Harmaline.Experimental
GliclazideHarmaline may increase the hypoglycemic activities of Gliclazide.Approved
GlimepirideHarmaline may increase the hypoglycemic activities of Glimepiride.Approved
GlipizideHarmaline may increase the hypoglycemic activities of Glipizide.Approved
GlyburideHarmaline may increase the hypoglycemic activities of Glyburide.Approved
GuanabenzHarmaline may increase the hypotensive activities of Guanabenz.Approved, Investigational
GuanadrelHarmaline may increase the hypotensive activities of Guanadrel.Approved
GuanazodineHarmaline may increase the hypotensive activities of Guanazodine.Experimental
GuanethidineHarmaline may increase the hypotensive activities of Guanethidine.Approved
GuanfacineHarmaline may increase the hypotensive activities of Guanfacine.Approved, Investigational
GuanoclorHarmaline may increase the hypotensive activities of Guanoclor.Experimental
GuanoxabenzHarmaline may increase the hypotensive activities of Guanoxabenz.Experimental
GuanoxanHarmaline may increase the hypotensive activities of Guanoxan.Experimental
HeroinThe risk or severity of adverse effects can be increased when Heroin is combined with Harmaline.Approved, Illicit, Investigational
HexamethoniumHarmaline may increase the hypotensive activities of Hexamethonium.Experimental
HydracarbazineHarmaline may increase the hypertensive activities of Hydracarbazine.Experimental
HydralazineHarmaline may increase the hypotensive activities of Hydralazine.Approved
HydrochlorothiazideHarmaline may increase the hypotensive activities of Hydrochlorothiazide.Approved, Vet Approved
HydrocodoneThe risk or severity of adverse effects can be increased when Harmaline is combined with Hydrocodone.Approved, Illicit
HydroflumethiazideHarmaline may increase the hypotensive activities of Hydroflumethiazide.Approved, Investigational
HydromorphoneThe risk or severity of adverse effects can be increased when Harmaline is combined with Hydromorphone.Approved, Illicit
HydroxyamphetamineThe risk or severity of adverse effects can be increased when Hydroxyamphetamine is combined with Harmaline.Approved
ImidaprilHarmaline may increase the hypotensive activities of Imidapril.Investigational
ImipramineHarmaline may increase the serotonergic activities of Imipramine.Approved
IndacaterolThe risk or severity of adverse effects can be increased when Harmaline is combined with Indacaterol.Approved
IndalpineThe risk or severity of adverse effects can be increased when Indalpine is combined with Harmaline.Investigational, Withdrawn
IndapamideHarmaline may increase the hypotensive activities of Indapamide.Approved
IndenololHarmaline may increase the hypotensive activities of Indenolol.Withdrawn
IndoraminHarmaline may increase the hypotensive activities of Indoramin.Withdrawn
Insulin AspartHarmaline may increase the hypoglycemic activities of Insulin Aspart.Approved
Insulin DetemirHarmaline may increase the hypoglycemic activities of Insulin Detemir.Approved
Insulin GlargineHarmaline may increase the hypoglycemic activities of Insulin Glargine.Approved
Insulin GlulisineHarmaline may increase the hypoglycemic activities of Insulin Glulisine.Approved
Insulin HumanHarmaline may increase the hypoglycemic activities of Insulin Human.Approved, Investigational
Insulin LisproHarmaline may increase the hypoglycemic activities of Insulin Lispro.Approved
Iofetamine I-123The risk or severity of adverse effects can be increased when Iofetamine I-123 is combined with Harmaline.Approved
IprindoleHarmaline may increase the serotonergic activities of Iprindole.Experimental
IproclozideHarmaline may increase the hypertensive activities of Iproclozide.Withdrawn
IproniazidIproniazid may increase the hypertensive activities of Harmaline.Withdrawn
IrbesartanHarmaline may increase the hypotensive activities of Irbesartan.Approved, Investigational
IsocarboxazidIsocarboxazid may increase the hypertensive activities of Harmaline.Approved
IsoetarineThe risk or severity of adverse effects can be increased when Harmaline is combined with Isoetarine.Approved
IsomethepteneThe risk or severity of adverse effects can be increased when Harmaline is combined with Isometheptene.Approved
IsoprenalineThe risk or severity of adverse effects can be increased when Harmaline is combined with Isoprenaline.Approved
IsradipineHarmaline may increase the hypotensive activities of Isradipine.Approved
KetanserinHarmaline may increase the hypotensive activities of Ketanserin.Investigational
KetobemidoneThe risk or severity of adverse effects can be increased when Ketobemidone is combined with Harmaline.Approved, Investigational
L-TryptophanThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Harmaline.Approved, Nutraceutical, Withdrawn
LabetalolHarmaline may increase the hypotensive activities of Labetalol.Approved
LacidipineHarmaline may increase the hypotensive activities of Lacidipine.Approved, Investigational
LatanoprostHarmaline may increase the hypotensive activities of Latanoprost.Approved, Investigational
LercanidipineHarmaline may increase the hypotensive activities of Lercanidipine.Approved, Investigational
LevodopaThe risk or severity of adverse effects can be increased when Levodopa is combined with Harmaline.Approved
Levomethadyl AcetateThe risk or severity of adverse effects can be increased when Levomethadyl Acetate is combined with Harmaline.Approved, Investigational
LevomilnacipranThe risk or severity of adverse effects can be increased when Levomilnacipran is combined with Harmaline.Approved
LevonordefrinHarmaline may increase the hypertensive activities of Levonordefrin.Approved
LevorphanolThe risk or severity of adverse effects can be increased when Levorphanol is combined with Harmaline.Approved
LevosalbutamolThe risk or severity of adverse effects can be increased when Harmaline is combined with Levosalbutamol.Approved
LinezolidThe risk or severity of adverse effects can be increased when Harmaline is combined with Linezolid.Approved, Investigational
LinsidomineHarmaline may increase the hypotensive activities of Linsidomine.Experimental
LiraglutideHarmaline may increase the hypoglycemic activities of Liraglutide.Approved
LisdexamfetamineThe risk or severity of adverse effects can be increased when Lisdexamfetamine is combined with Harmaline.Approved, Investigational
LisinoprilHarmaline may increase the hypotensive activities of Lisinopril.Approved, Investigational
LisurideThe metabolism of Lisuride can be decreased when combined with Harmaline.Approved, Investigational
LithiumThe risk or severity of adverse effects can be increased when Harmaline is combined with Lithium.Approved
LofentanilThe risk or severity of adverse effects can be increased when Lofentanil is combined with Harmaline.Illicit
LofepramineHarmaline may increase the serotonergic activities of Lofepramine.Experimental
LofexidineHarmaline may increase the hypotensive activities of Lofexidine.Approved, Investigational
LosartanHarmaline may increase the hypotensive activities of Losartan.Approved
MacitentanHarmaline may increase the hypotensive activities of Macitentan.Approved
ManidipineHarmaline may increase the hypotensive activities of Manidipine.Approved, Investigational
MaprotilineThe risk or severity of adverse effects can be increased when Maprotiline is combined with Harmaline.Approved
MebanazineHarmaline may increase the hypertensive activities of Mebanazine.Withdrawn
MecamylamineHarmaline may increase the hypotensive activities of Mecamylamine.Approved
MecaserminHarmaline may increase the hypoglycemic activities of Mecasermin.Approved, Investigational
MephedroneThe risk or severity of adverse effects can be increased when Mephedrone is combined with Harmaline.Investigational
MephentermineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Harmaline.Approved
MeptazinolThe risk or severity of adverse effects can be increased when Meptazinol is combined with Harmaline.Experimental
MequitazineHarmaline may increase the anticholinergic activities of Mequitazine.Approved
MetaraminolHarmaline may increase the hypertensive activities of Metaraminol.Approved, Investigational
MetforminHarmaline may increase the hypoglycemic activities of Metformin.Approved
MethadoneThe risk or severity of adverse effects can be increased when Harmaline is combined with Methadone.Approved
Methadyl AcetateThe risk or severity of adverse effects can be increased when Methadyl Acetate is combined with Harmaline.Approved, Illicit
MethamphetamineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Harmaline.Approved, Illicit
MethoserpidineHarmaline may increase the hypotensive activities of Methoserpidine.Experimental
MethoxamineHarmaline may increase the hypertensive activities of Methoxamine.Approved, Investigational
MethoxyphenamineThe risk or severity of adverse effects can be increased when Methoxyphenamine is combined with Harmaline.Experimental
MethyldopaThe risk or severity of adverse effects can be increased when Harmaline is combined with Methyldopa.Approved
MethylecgonineThe risk or severity of adverse effects can be increased when Methylecgonine is combined with Harmaline.Experimental
Methylene blueHarmaline may increase the serotonergic activities of Methylene blue.Approved, Investigational
MethylphenidateHarmaline may increase the hypertensive activities of Methylphenidate.Approved, Investigational
MetipranololHarmaline may increase the hypotensive activities of Metipranolol.Approved
MetolazoneHarmaline may increase the hypotensive activities of Metolazone.Approved
MetoprololHarmaline may increase the hypotensive activities of Metoprolol.Approved, Investigational
MetyrosineHarmaline may increase the hypotensive activities of Metyrosine.Approved
MianserinHarmaline may increase the neurotoxic activities of Mianserin.Approved, Investigational
MibefradilHarmaline may increase the hypotensive activities of Mibefradil.Investigational, Withdrawn
MidodrineHarmaline may increase the hypertensive activities of Midodrine.Approved
MidomafetamineThe risk or severity of adverse effects can be increased when Midomafetamine is combined with Harmaline.Experimental, Illicit, Investigational
MifepristoneHarmaline may increase the hypoglycemic activities of Mifepristone.Approved, Investigational
MiglitolHarmaline may increase the hypoglycemic activities of Miglitol.Approved
MilnacipranThe risk or severity of adverse effects can be increased when Milnacipran is combined with Harmaline.Approved
MinaprineMinaprine may increase the hypertensive activities of Harmaline.Approved
MinoxidilHarmaline may increase the hypotensive activities of Minoxidil.Approved
MirtazapineHarmaline may increase the central neurotoxic activities of Mirtazapine.Approved
MMDAThe risk or severity of adverse effects can be increased when MMDA is combined with Harmaline.Experimental, Illicit
MoclobemideThe risk or severity of adverse effects can be increased when Harmaline is combined with Moclobemide.Approved
MoexiprilHarmaline may increase the hypotensive activities of Moexipril.Approved
MorphineThe risk or severity of adverse effects can be increased when Harmaline is combined with Morphine.Approved, Investigational
MoxonidineHarmaline may increase the hypotensive activities of Moxonidine.Approved, Investigational
MuzolimineHarmaline may increase the hypotensive activities of Muzolimine.Experimental
NadololHarmaline may increase the hypotensive activities of Nadolol.Approved
NaftopidilHarmaline may increase the hypotensive activities of Naftopidil.Investigational
NalbuphineThe risk or severity of adverse effects can be increased when Nalbuphine is combined with Harmaline.Approved
NaratriptanThe serum concentration of Naratriptan can be increased when it is combined with Harmaline.Approved, Investigational
NateglinideHarmaline may increase the hypoglycemic activities of Nateglinide.Approved, Investigational
NebivololHarmaline may increase the hypotensive activities of Nebivolol.Approved, Investigational
NefazodoneThe risk or severity of adverse effects can be increased when Nefazodone is combined with Harmaline.Approved, Withdrawn
NialamideNialamide may increase the hypertensive activities of Harmaline.Withdrawn
NicardipineHarmaline may increase the hypotensive activities of Nicardipine.Approved
NicorandilHarmaline may increase the hypotensive activities of Nicorandil.Approved, Investigational
NiguldipineHarmaline may increase the hypotensive activities of Niguldipine.Experimental
NilvadipineHarmaline may increase the hypotensive activities of Nilvadipine.Approved, Investigational
NimodipineHarmaline may increase the hypotensive activities of Nimodipine.Approved
NisoldipineHarmaline may increase the hypotensive activities of Nisoldipine.Approved
NitrendipineHarmaline may increase the hypotensive activities of Nitrendipine.Approved, Investigational
NitroprussideHarmaline may increase the hypotensive activities of Nitroprusside.Approved
NorepinephrineHarmaline may increase the hypertensive activities of Norepinephrine.Approved
NormethadoneThe risk or severity of adverse effects can be increased when Normethadone is combined with Harmaline.Approved, Illicit
NortriptylineHarmaline may increase the serotonergic activities of Nortriptyline.Approved
OctamoxinHarmaline may increase the hypertensive activities of Octamoxin.Withdrawn
OlanzapineThe risk or severity of adverse effects can be increased when Harmaline is combined with Olanzapine.Approved, Investigational
OlmesartanHarmaline may increase the hypotensive activities of Olmesartan.Approved, Investigational
OlodaterolThe risk or severity of adverse effects can be increased when Harmaline is combined with Olodaterol.Approved
OmapatrilatHarmaline may increase the hypotensive activities of Omapatrilat.Investigational
OpipramolHarmaline may increase the serotonergic activities of Opipramol.Investigational
OpiumThe risk or severity of adverse effects can be increased when Opium is combined with Harmaline.Approved, Illicit
OrciprenalineThe risk or severity of adverse effects can be increased when Harmaline is combined with Orciprenaline.Approved
OxprenololHarmaline may increase the hypotensive activities of Oxprenolol.Approved
OxycodoneThe risk or severity of adverse effects can be increased when Harmaline is combined with Oxycodone.Approved, Illicit, Investigational
OxymorphoneThe risk or severity of adverse effects can be increased when Oxymorphone is combined with Harmaline.Approved, Investigational, Vet Approved
PargylineHarmaline may increase the hypotensive activities of Pargyline.Approved
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Harmaline.Approved, Investigational
PenbutololHarmaline may increase the hypotensive activities of Penbutolol.Approved, Investigational
PentamidineHarmaline may increase the hypoglycemic activities of Pentamidine.Approved
PentazocineThe risk or severity of adverse effects can be increased when Pentazocine is combined with Harmaline.Approved, Vet Approved
PentoliniumHarmaline may increase the hypotensive activities of Pentolinium.Approved
PergolideThe metabolism of Pergolide can be decreased when combined with Harmaline.Approved, Investigational, Vet Approved, Withdrawn
PerindoprilHarmaline may increase the hypotensive activities of Perindopril.Approved
PethidineHarmaline may increase the serotonergic activities of Pethidine.Approved
PhenazocineThe risk or severity of adverse effects can be increased when Phenazocine is combined with Harmaline.Experimental
PhenelzinePhenelzine may increase the hypertensive activities of Harmaline.Approved
PheniprazineHarmaline may increase the hypertensive activities of Pheniprazine.Withdrawn
PhenoperidineThe risk or severity of adverse effects can be increased when Phenoperidine is combined with Harmaline.Experimental
PhenoxybenzamineHarmaline may increase the hypotensive activities of Phenoxybenzamine.Approved
PhenoxypropazineHarmaline may increase the hypertensive activities of Phenoxypropazine.Withdrawn
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Harmaline.Approved, Illicit
PhentolamineHarmaline may increase the hypotensive activities of Phentolamine.Approved
PhenylephrineHarmaline may increase the hypertensive activities of Phenylephrine.Approved
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Harmaline is combined with Phenylpropanolamine.Approved, Vet Approved, Withdrawn
PholcodinePholcodine may increase the serotonergic activities of Harmaline.Approved, Illicit
PiclozotanThe metabolism of Piclozotan can be decreased when combined with Harmaline.Investigational
PinacidilHarmaline may increase the hypotensive activities of Pinacidil.Withdrawn
PindololHarmaline may increase the hypotensive activities of Pindolol.Approved
PioglitazoneHarmaline may increase the hypoglycemic activities of Pioglitazone.Approved, Investigational
PirbuterolThe risk or severity of adverse effects can be increased when Harmaline is combined with Pirbuterol.Approved
PiritramideThe risk or severity of adverse effects can be increased when Piritramide is combined with Harmaline.Investigational
PirlindolePirlindole may increase the hypertensive activities of Harmaline.Approved
PivhydrazineHarmaline may increase the hypertensive activities of Pivhydrazine.Withdrawn
PizotifenHarmaline may increase the anticholinergic activities of Pizotifen.Approved
Platelet Activating FactorHarmaline may increase the hypotensive activities of Platelet Activating Factor.Experimental
PolythiazideHarmaline may increase the hypotensive activities of Polythiazide.Approved
PramlintideHarmaline may increase the hypoglycemic activities of Pramlintide.Approved, Investigational
PrazosinHarmaline may increase the hypotensive activities of Prazosin.Approved
ProcarbazineHarmaline may increase the hypertensive activities of Procarbazine.Approved
ProcaterolThe risk or severity of adverse effects can be increased when Harmaline is combined with Procaterol.Approved, Investigational
PropranololHarmaline may increase the hypotensive activities of Propranolol.Approved, Investigational
ProtriptylineHarmaline may increase the serotonergic activities of Protriptyline.Approved
PRX-00023The metabolism of PRX-00023 can be decreased when combined with Harmaline.Investigational
PseudoephedrineThe risk or severity of adverse effects can be increased when Pseudoephedrine is combined with Harmaline.Approved
QuinaprilHarmaline may increase the hypotensive activities of Quinapril.Approved, Investigational
QuinineHarmaline may increase the hypoglycemic activities of Quinine.Approved
RamiprilHarmaline may increase the hypotensive activities of Ramipril.Approved
RasagilineRasagiline may increase the hypertensive activities of Harmaline.Approved
RemifentanilThe risk or severity of adverse effects can be increased when Remifentanil is combined with Harmaline.Approved
RemikirenHarmaline may increase the hypotensive activities of Remikiren.Approved
RepaglinideHarmaline may increase the hypoglycemic activities of Repaglinide.Approved, Investigational
RescinnamineHarmaline may increase the hypotensive activities of Rescinnamine.Approved
ReserpineThe risk or severity of adverse effects can be increased when Harmaline is combined with Reserpine.Approved, Investigational
RilmenidineHarmaline may increase the hypotensive activities of Rilmenidine.Investigational
RiociguatHarmaline may increase the hypotensive activities of Riociguat.Approved
RitobegronThe risk or severity of adverse effects can be increased when Ritobegron is combined with Harmaline.Investigational
RitodrineThe risk or severity of adverse effects can be increased when Harmaline is combined with Ritodrine.Approved, Investigational
RizatriptanThe serum concentration of Rizatriptan can be increased when it is combined with Harmaline.Approved
RopiniroleThe metabolism of Ropinirole can be decreased when combined with Harmaline.Approved, Investigational
RosiglitazoneHarmaline may increase the hypoglycemic activities of Rosiglitazone.Approved, Investigational
SafrazineHarmaline may increase the hypertensive activities of Safrazine.Withdrawn
SalbutamolThe risk or severity of adverse effects can be increased when Harmaline is combined with Salbutamol.Approved, Vet Approved
SalmeterolThe risk or severity of adverse effects can be increased when Harmaline is combined with Salmeterol.Approved
SaprisartanHarmaline may increase the hypotensive activities of Saprisartan.Experimental
SaxagliptinHarmaline may increase the hypoglycemic activities of Saxagliptin.Approved
SelegilineSelegiline may increase the hypertensive activities of Harmaline.Approved, Investigational, Vet Approved
SelexipagHarmaline may increase the hypotensive activities of Selexipag.Approved
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Harmaline.Approved
SitagliptinHarmaline may increase the hypoglycemic activities of Sitagliptin.Approved, Investigational
SitaxentanHarmaline may increase the hypotensive activities of Sitaxentan.Approved, Investigational, Withdrawn
SpiraprilHarmaline may increase the hypotensive activities of Spirapril.Approved
SufentanilThe risk or severity of adverse effects can be increased when Sufentanil is combined with Harmaline.Approved, Investigational
SulfadiazineHarmaline may increase the hypoglycemic activities of Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleHarmaline may increase the hypoglycemic activities of Sulfamethoxazole.Approved
SulfisoxazoleHarmaline may increase the hypoglycemic activities of Sulfisoxazole.Approved, Vet Approved
SumatriptanThe serum concentration of Sumatriptan can be increased when it is combined with Harmaline.Approved, Investigational
SunitinibHarmaline may increase the hypoglycemic activities of Sunitinib.Approved, Investigational
TalinololHarmaline may increase the hypotensive activities of Talinolol.Investigational
TapentadolThe risk or severity of adverse effects can be increased when Tapentadol is combined with Harmaline.Approved
TelmisartanHarmaline may increase the hypotensive activities of Telmisartan.Approved, Investigational
TemocaprilHarmaline may increase the hypotensive activities of Temocapril.Experimental, Investigational
TerbutalineThe risk or severity of adverse effects can be increased when Harmaline is combined with Terbutaline.Approved
TerlipressinHarmaline may increase the hypotensive activities of Terlipressin.Approved, Investigational
Testosterone PropionateThe risk or severity of adverse effects can be increased when Testosterone Propionate is combined with Harmaline.Approved, Vet Approved
TetrabenazineThe risk or severity of adverse effects can be increased when Tetrabenazine is combined with Harmaline.Approved
TetrahydropalmatineHarmaline may increase the hypotensive activities of Tetrahydropalmatine.Investigational
TetryzolineHarmaline may increase the hypertensive activities of Tetryzoline.Approved
TheodrenalineHarmaline may increase the hypotensive activities of Theodrenaline.Investigational
TianeptineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Harmaline.Approved, Investigational
TiboloneHarmaline may increase the hypotensive activities of Tibolone.Approved, Investigational
TicrynafenHarmaline may increase the hypotensive activities of Ticrynafen.Withdrawn
TilidineThe risk or severity of adverse effects can be increased when Tilidine is combined with Harmaline.Experimental
TimololHarmaline may increase the hypotensive activities of Timolol.Approved
TolazamideHarmaline may increase the hypoglycemic activities of Tolazamide.Approved
TolazolineHarmaline may increase the hypotensive activities of Tolazoline.Approved, Vet Approved
TolbutamideHarmaline may increase the hypoglycemic activities of Tolbutamide.Approved
TolcaponeThe risk or severity of adverse effects can be increased when Tolcapone is combined with Harmaline.Approved, Withdrawn
TolonidineHarmaline may increase the hypotensive activities of Tolonidine.Experimental
ToloxatoneToloxatone may increase the hypertensive activities of Harmaline.Approved
TorasemideHarmaline may increase the hypotensive activities of Torasemide.Approved
TramadolTramadol may increase the neuroexcitatory activities of Harmaline.Approved, Investigational
TrandolaprilHarmaline may increase the hypotensive activities of Trandolapril.Approved
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypertensive activities of Harmaline.Experimental
TranylcypromineTranylcypromine may increase the hypertensive activities of Harmaline.Approved
TravoprostHarmaline may increase the hypotensive activities of Travoprost.Approved
TrazodoneThe risk or severity of adverse effects can be increased when Harmaline is combined with Trazodone.Approved, Investigational
TreprostinilHarmaline may increase the hypotensive activities of Treprostinil.Approved, Investigational
TrichlormethiazideHarmaline may increase the hypotensive activities of Trichlormethiazide.Approved, Vet Approved
TrimazosinHarmaline may increase the hypotensive activities of Trimazosin.Experimental
TrimethaphanHarmaline may increase the hypotensive activities of Trimethaphan.Approved, Investigational
TrimipramineHarmaline may increase the serotonergic activities of Trimipramine.Approved
UnoprostoneHarmaline may increase the hypotensive activities of Unoprostone.Approved
UrapidilHarmaline may increase the hypotensive activities of Urapidil.Investigational
ValsartanHarmaline may increase the hypotensive activities of Valsartan.Approved, Investigational
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Harmaline.Approved
VilanterolThe risk or severity of adverse effects can be increased when Harmaline is combined with Vilanterol.Approved
VilazodoneThe metabolism of Vilazodone can be decreased when combined with Harmaline.Approved
VincamineHarmaline may increase the hypotensive activities of Vincamine.Experimental
VinpocetineHarmaline may increase the hypotensive activities of Vinpocetine.Investigational
VortioxetineThe metabolism of Vortioxetine can be decreased when combined with Harmaline.Approved
XipamideHarmaline may increase the hypotensive activities of Xipamide.Experimental
XylometazolineHarmaline may increase the hypotensive activities of Xylometazoline.Approved
ZimelidineThe risk or severity of adverse effects can be increased when Zimelidine is combined with Harmaline.Withdrawn
ZofenoprilHarmaline may increase the hypotensive activities of Zofenopril.Experimental
ZolmitriptanThe serum concentration of Zolmitriptan can be increased when it is combined with Harmaline.Approved, Investigational
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB30310
KEGG Compound
C06536
PubChem Compound
5280951
PubChem Substance
347829327
ChemSpider
10211258
BindingDB
50029799
ChEBI
28172
ChEMBL
CHEMBL340807

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
PropertyValueSource
Water Solubility0.0576 mg/mLALOGPS
logP2.61ALOGPS
logP1.67ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)14.95ChemAxon
pKa (Strongest Basic)6.46ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.38 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity64.15 m3·mol-1ChemAxon
Polarizability24.2 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-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 compounds
show 1 more
Substituents
Harmaline / Harman / Beta-carboline / Pyridoindole / 3-alkylindole / Indole or derivatives / Indole / Anisole / Alkyl aryl ether / Benzenoid
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
harmala alkaloid (CHEBI:28172) / Indole alkaloids (C06536) / an alkaloid (CPD-9939)

Targets

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
  1. 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 December 12, 2017 10:05