One of the catecholamine neurotransmitters in the brain. It is derived from tyrosine and is the precursor to norepinephrine and epinephrine. Dopamine is a major transmitter in the extrapyramidal system of the brain, and important in regulating movement. A family of receptors (receptors, dopamine) mediate its action.

Structure

Similar Structures

Synonyms

2-(3,4-dihydroxyphenyl)ethylamine
3-Hydroxytyramine
3,4-Dihydroxyphenethylamine
4-(2-aminoethyl)-1,2-benzenediol
4-(2-Aminoethyl)benzene-1,2-diol
4-(2-aminoethyl)catechol
4-(2-aminoethyl)pyrocatechol
Dopamina
Dopamine
Dopaminum
Oxytyramine

External IDs

NSC-173182

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Dopamine hydrochloride	7L3E358N9L	62-31-7	CTENFNNZBMHDDG-UHFFFAOYSA-N

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Unlock Additional Data
Dopamine Hci	Injection, solution, concentrate	40 mg/1mL	Intravenous	Hf Acquisition Co. Llc, Dba Health First	2018-08-23	Not applicable
Dopamine Hci	Injection, solution, concentrate	40 mg/1mL	Intravenous	HF Acquisition Co LLC, DBA HealthFirst	2018-09-19	Not applicable
Dopamine Hci In 5% Dextrose	Injection, solution	1.6 mg/1mL	Intravenous	HF Acquisition Co LLC, DBA HealthFirst	2019-12-12	Not applicable
Dopamine HCl Inj 4%	Liquid		Intravenous	International Medication Systems, Limited	1980-12-31	1997-08-15
DOPamine Hydrochloride	Injection, solution, concentrate	40 mg/1mL	Intravenous	Hospira, Inc.	2005-08-25	Not applicable
Dopamine Hydrochloride	Injection, solution, concentrate	40 mg/1mL	Intravenous	General Injectables and Vaccines, Inc.	2015-09-18	Not applicable
DOPamine Hydrochloride	Injection, solution, concentrate	40 mg/1mL	Intravenous	Cardinal Health	1981-05-19	Not applicable
Dopamine Hydrochloride	Injection, solution, concentrate	40 mg/1mL	Intravenous	General Injectables & Vaccines, Inc	2010-08-01	Not applicable
Dopamine Hydrochloride	Injection, solution	1.6 mg/1mL	Intravenous	HF Acquisition Co LLC, DBA HealthFirst	2018-10-19	Not applicable
DOPamine Hydrochloride	Injection, solution, concentrate	40 mg/1mL	Intravenous	Remedy Repack	2015-01-23	2016-02-05

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Dopamine	Injection, solution	80 mg/1mL	Intravenous	General Injectables & Vaccines	2010-04-01	2014-09-01
Dopamine HCl	Injection, solution	80 mg/1mL	Intravenous	American Regent	1990-09-30	Not applicable
Dopamine HCl	Injection, solution	40 mg/1mL	Intravenous	American Regent	1990-09-30	Not applicable
Dopamine HCl	Injection, solution	160 mg/1mL	Intravenous	American Regent	1990-09-30	Not applicable
Dopamine HCl	Injection, solution	80 mg/1mL	Intravenous	Cardinal Health	1990-09-30	Not applicable
Dopamine HCl	Injection, solution	80 mg/1mL	Intravenous	Physicians Total Care, Inc.	1990-09-30	2007-06-30
Dopamine HCl	Injection, solution	40 mg/1mL	Intravenous	Cardinal Health	1987-02-11	Not applicable
Dopamine Hydrochloride	Injection	40 mg/1mL	Intravenous	West-Ward Pharmaceuticals Corp	2018-04-11	Not applicable
Dopamine Hydrochloride	Injection	80 mg/1mL	Intravenous	West-Ward Pharmaceuticals Corp	2018-04-11	Not applicable
Dopamine Hydrochloride	Injection	40 mg/1mL	Intravenous	West-Ward Pharmaceuticals Corp	2018-04-11	Not applicable

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Dopamine HCl 0.8mg/ml Dextrose 5% Inj USP	Dopamine hydrochloride (.8 mg) + Dextrose, unspecified form (50 mg)	Solution	Intravenous	Baxter Laboratories	1992-12-31	Not applicable
Dopamine HCl 1.6mg/ml Dextrose 5% Inj USP	Dopamine hydrochloride (1.6 mg) + Dextrose, unspecified form (50 mg)	Solution	Intravenous	Baxter Laboratories	1990-12-31	Not applicable
Dopamine HCl 3.2mg/ml Dextrose 5% Inj USP	Dopamine hydrochloride (3.2 mg) + Dextrose, unspecified form (50 mg)	Solution	Intravenous	Baxter Laboratories	1990-12-31	Not applicable
Dopamine Hydrochloride and 5% Dextrose Injection USP	Dopamine hydrochloride (0.8 mg) + Dextrose, unspecified form (50 mg)	Solution	Intravenous	Hospira Healthcare Ulc	1986-12-31	2018-11-30
Dopamine Hydrochloride and 5% Dextrose Injection USP	Dopamine hydrochloride (1.6 mg) + Dextrose, unspecified form (50 mg)	Solution	Intravenous	Hospira Healthcare Ulc	1986-12-31	2018-11-30
Dopamine Hydrochloride and 5% Dextrose Injection USP	Dopamine hydrochloride (3.2 mg) + Dextrose, unspecified form (50 mg)	Solution	Intravenous	Hospira Healthcare Ulc	1991-12-31	2018-11-30
Dopamine Hydrochloride in Dextrose	Dopamine hydrochloride (160 mg/100mL) + D-glucose monohydrate (5 g/100mL)	Injection, solution	Intravenous	B. Braun Medical Inc.	2007-03-01	2012-09-01
Dopamine Hydrochloride in Dextrose	Dopamine hydrochloride (160 mg/100mL) + D-glucose monohydrate (5 g/100mL)	Injection, solution	Intravenous	B. Braun Medical Inc.	2007-03-01	2012-09-01
Dopamine Hydrochloride in Dextrose	Dopamine hydrochloride (80 mg/100mL) + D-glucose monohydrate (5 g/100mL)	Injection, solution	Intravenous	B. Braun Medical Inc.	2007-03-01	2012-09-01
Dopamine Hydrochloride in Dextrose	Dopamine hydrochloride (80 mg/100mL) + D-glucose monohydrate (5 g/100mL)	Injection, solution	Intravenous	B. Braun Medical Inc.	2007-03-01	2012-09-01

International/Other Brands

Intropin / Revimine

Categories

UNII

VTD58H1Z2X

CAS number

51-61-6

Weight

Average: 153.1784
Monoisotopic: 153.078978601

Chemical Formula

C₈H₁₁NO₂

InChI Key

VYFYYTLLBUKUHU-UHFFFAOYSA-N

InChI

InChI=1S/C8H11NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,10-11H,3-4,9H2

IUPAC Name

4-(2-aminoethyl)benzene-1,2-diol

SMILES

NCCC1=CC(O)=C(O)C=C1

Pharmacology

Indication

For the correction of hemodynamic imbalances present in the shock syndrome due to myocardial infarction, trauma, endotoxic septicemia, open-heart surgery, renal failure, and chronic cardiac decompensation as in congestive failure

Associated Conditions

Pharmacodynamics

Dopamine is a natural catecholamine formed by the decarboxylation of 3,4-dihydroxyphenylalanine (DOPA). It is a precursor to norepinephrine in noradrenergic nerves and is also a neurotransmitter in certain areas of the central nervous system, especially in the nigrostriatal tract, and in a few peripheral sympathetic nerves. Dopamine produces positive chronotropic and inotropic effects on the myocardium, resulting in increased heart rate and cardiac contractility. This is accomplished directly by exerting an agonist action on beta-adrenoceptors and indirectly by causing release of norepinephrine from storage sites in sympathetic nerve endings.

Mechanism of action

Dopamine is a precursor to norepinephrine in noradrenergic nerves and is also a neurotransmitter in certain areas of the central nervous system. Dopamine produces positive chronotropic and inotropic effects on the myocardium, resulting in increased heart rate and cardiac contractility. This is accomplished directly by exerting an agonist action on beta-adrenoceptors and indirectly by causing release of norepinephrine from storage sites in sympathetic nerve endings. In the brain, dopamine actas as an agonist to the five dopamine receptor subtypes (D!, D2, D3, D4, D5).

Target	Actions	Organism
ADopamine D2 receptor	agonist	Humans
ADopamine D1 receptor	agonist	Humans
ADopamine D5 receptor	agonist	Humans
ADopamine D3 receptor	agonist	Humans
ADopamine D4 receptor	agonist	Humans
ASodium-dependent dopamine transporter	inducer	Humans
ADopamine beta-hydroxylase	ligand	Humans
U5-hydroxytryptamine receptor 1A	binder	Humans
U5-hydroxytryptamine receptor 7	binder	Humans
UD(1) dopamine receptor	agonist	Humans
USodium-dependent noradrenaline transporter	inhibitor	Humans
USodium-dependent serotonin transporter	inhibitor	Humans
U5-hydroxytryptamine receptor 3A	Not Available	Humans
U5-hydroxytryptamine receptor 3B	Not Available	Humans
USuperoxide dismutase [Cu-Zn]	Not Available	Humans
USynaptic vesicular amine transporter	Not Available	Humans

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Additional Data Available

Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available

Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available

Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Dopamine is rapidly absorbed from the small intestine.

Volume of distribution

Not Available

Protein binding

No information currently available on protein binding.

Metabolism

Biotransformation of dopamine proceeds rapidly to yield the principal excretion products, 3-4-dihydroxy-phenylacetic acid (DOPAC) and 3-methoxy-4-hydroxy-phenylacetic acid (homovanillic acid, HVA).

Route of elimination

It has been reported that about 80% of the drug is excreted in the urine within 24 hours, primarily as HVA and its sulfate and glucuronide conjugates and as 3,4-dihydroxyphenylacetic acid. A very small portion is excreted unchanged.

Half life

2 minutes

Clearance

Not Available

Toxicity

LD₅₀ oral mice = 1460 mg/kg, LD₅₀ oral rats = 1780 mg/kg. Spasm or closing of eyelids, nausea, vomiting, cardiac arrhythmias, involuntary movements of the body including the face, tongue, arms, hand, head, and upper body; hypotension, haemolytic anaemia, urinary retention, duodenal ulcer, sialorrhea, ataxia, abdominal pain, dry mouth, nightmares, tachypnoea, bruxism, confusion, and insomnia.

Affected organisms

Humans and other mammals

Pathways

Pathway	Category
Aromatic L-Aminoacid Decarboxylase Deficiency	Disease
Benzocaine Action Pathway	Drug action
Bupivacaine Action Pathway	Drug action
Lidocaine (Local Anaesthetic) Action Pathway	Drug action
Proparacaine Action Pathway	Drug action
Codeine Action Pathway	Drug action
Hydromorphone Action Pathway	Drug action
Fentanyl Action Pathway	Drug action
Sufentanil Action Pathway	Drug action
Methadyl Acetate Action Pathway	Drug action
Dimethylthiambutene Action Pathway	Drug action
Dihydromorphine Action Pathway	Drug action
Ketobemidone Action Pathway	Drug action
Alkaptonuria	Disease
Hawkinsinuria	Disease
Dopamine Activation of Neurological Reward System	Signaling
Oxybuprocaine Action Pathway	Drug action
Morphine Action Pathway	Drug action
Hydrocodone Action Pathway	Drug action
Oxymorphone Action Pathway	Drug action
Remifentanil Action Pathway	Drug action
Fluoxetine Action Pathway	Drug action
Nicotine Action Pathway	Drug action
Tyrosinemia, Transient, of the Newborn	Disease
Tyrosine Hydroxylase Deficiency	Disease
Dopamine beta-Hydroxylase Deficiency	Disease
Monoamine Oxidase-A Deficiency (MAO-A)	Disease
Propoxyphene Action Pathway	Drug action
Anileridine Action Pathway	Drug action
3-Methylthiofentanyl Action Pathway	Drug action

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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1-benzylimidazole	The risk or severity of hypertension can be increased when Dopamine is combined with 1-benzylimidazole.
2,5-Dimethoxy-4-ethylamphetamine	The risk or severity of adverse effects can be increased when Dopamine is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamine	The risk or severity of adverse effects can be increased when Dopamine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthine	The risk or severity of adverse effects can be increased when Dopamine is combined with 3-isobutyl-1-methyl-7H-xanthine.
3,5-diiodothyropropionic acid	The risk or severity of adverse effects can be increased when Dopamine is combined with 3,5-diiodothyropropionic acid.
3,5-Diiodotyrosine	The risk or severity of adverse effects can be increased when Dopamine is combined with 3,5-Diiodotyrosine.
3,5-Dinitrocatechol	The metabolism of Dopamine can be decreased when combined with 3,5-Dinitrocatechol.
4-Bromo-2,5-dimethoxyamphetamine	The risk or severity of adverse effects can be increased when Dopamine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-Methoxyamphetamine	The metabolism of Dopamine can be decreased when combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamine	The risk or severity of hypertension can be increased when Dopamine is combined with 5-methoxy-N,N-dimethyltryptamine.

Additional Data Available

Extended Description

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

A severity rating for each drug interaction, from minor to major.

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Evidence Level

A rating for the strength of the evidence supporting each drug interaction.

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Action

An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions

Not Available

References

Synthesis Reference

Klaus Schoellkopf, Rudolf Albrecht, Manfred Lehmann, Gertrud Schroeder, "Novel dopamine derivatives, processes for their preparation, and their use as medicinal agents." U.S. Patent US4958026, issued February, 1972.

US4958026

General References

Barron AB, Maleszka R, Vander Meer RK, Robinson GE: Octopamine modulates honey bee dance behavior. Proc Natl Acad Sci U S A. 2007 Jan 30;104(5):1703-7. Epub 2007 Jan 19. [PubMed:17237217]
Giuliano F, Allard J: Dopamine and male sexual function. Eur Urol. 2001 Dec;40(6):601-8. [PubMed:11805404]
Giuliano F, Allard J: Dopamine and sexual function. Int J Impot Res. 2001 Aug;13 Suppl 3:S18-28. [PubMed:11477488]
Berridge KC, Robinson TE: What is the role of dopamine in reward: hedonic impact, reward learning, or incentive salience? Brain Res Brain Res Rev. 1998 Dec;28(3):309-69. [PubMed:9858756]
Pecina S, Cagniard B, Berridge KC, Aldridge JW, Zhuang X: Hyperdopaminergic mutant mice have higher "wanting" but not "liking" for sweet rewards. J Neurosci. 2003 Oct 15;23(28):9395-402. [PubMed:14561867]

External Links

Human Metabolome Database: HMDB0000073
KEGG Drug: D07870
KEGG Compound: C03758
PubChem Compound: 681
PubChem Substance: 46506043
ChemSpider: 661
BindingDB: 55121
RxNav: 3628
ChEBI: 18243
ChEMBL: CHEMBL59
ZINC: ZINC000000033882
Therapeutic Targets Database: DAP000212
PharmGKB: PA449396
Guide to Pharmacology: GtP Drug Page
PDBe Ligand: LDP
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Dopamine

ATC Codes

C01CA04 — Dopamine

AHFS Codes

12:12.08.08 — Selective Beta 1-adrenergic Agonists

PDB Entries

2a3r / 2qmz / 2vq5 / 3nk2 / 4a7v / 4dtz / 4du2 / 4dub / 4xp1 / 5log …

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MSDS

Download (72.1 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Treatment	Blood Pressures / Hypotension / Infant, Low Birth Weight / Infant, Small for Gestational Age / Infants, Premature / Newborn Infants	1
1	Completed	Treatment	Depressive Disorder and Anxiety Disorders / Depressive Disorders	1
1	Completed	Treatment	Hyperglycemia / Sepsis	1
1	Unknown Status	Treatment	Arterial hypoxia / Hypotension	1
1, 2	Active Not Recruiting	Treatment	Brain Diseases / Movement Disorders / Nervous System Diseases / Neuro-Degenerative Disease / Parkinson's Disease (PD)	1
1, 2	Completed	Treatment	Brain Diseases / Movement Disorders / Nervous System Diseases / Neurodegenerative Disorders / Parkinson's Disease (PD)	1
2	Completed	Treatment	Acute Heart Failure (AHF)	1
2	Completed	Treatment	Post Traumatic Stress Disorder (PTSD)	1
2	Recruiting	Treatment	Diabetic Macular Edema (DME) / Diabetic Retinopathy (DR)	1
2	Unknown Status	Treatment	Parkinson's Disease (PD)	1
2, 3	Completed	Treatment	Heart Failure	1
2, 3	Completed	Treatment	Liver Cirrhosis / Shock, Septic	1
2, 3	Completed	Treatment	Migraine	1
2, 3	Recruiting	Prevention	Transplant, Kidney	1
2, 3	Suspended	Prevention	Post-operative Cognitive Dysfunction	1
3	Completed	Treatment	Parkinson's Disease (PD)	1
3	Completed	Treatment	Shock	1
3	Completed	Treatment	Shock, Septic	1
3	Terminated	Treatment	Hypotension / Intraventricular Hemorrhage of Prematurity	1
4	Active Not Recruiting	Treatment	Arterial Hypotension	1
4	Completed	Prevention	Delirium	1
4	Completed	Treatment	Acromegaly	1
4	Completed	Treatment	ESRD / Transplantation, Kidney	1
4	Completed	Treatment	Ekbom Syndrome / Restless Legs Syndrome (RLS) / Willis-Ekbom Disease	1
4	Completed	Treatment	Head and Neck Carcinoma	1
4	Completed	Treatment	Heart Failure, Diastolic	1
4	Completed	Treatment	Parkinson's Disease (PD)	2
4	Not Yet Recruiting	Treatment	Children AKI Patients	1
4	Recruiting	Prevention	Renal Function	1
4	Recruiting	Treatment	Prolactin-Producing Pituitary Tumor / Prolactinoma	1
4	Recruiting	Treatment	Restless Legs Syndrome (RLS)	1
4	Suspended	Treatment	Acute Decompensated Heart Failure (ADHF)	1
4	Terminated	Treatment	Acute Decompensated Heart Failure (ADHF)	1
4	Terminated	Treatment	Stroke	1
4	Unknown Status	Treatment	Acute Heart Failure (AHF)	1
4	Unknown Status	Treatment	Dystonic Cerebral Palsy	1
4	Unknown Status	Treatment	Microcirculation / Severe Sepsis	1
Not Available	Active Not Recruiting	Other	Dependence, Cocaine	1
Not Available	Completed	Not Available	Neuro-Degenerative Disease	1
Not Available	Completed	Diagnostic	Renal Function Test, Urine Output, Lactate Level	1
Not Available	Completed	Prevention	Hypotension	1
Not Available	Completed	Treatment	Acute Kidney Injury (AKI)	1
Not Available	Completed	Treatment	Hypotension	1
Not Available	Completed	Treatment	Hypotension / Shock	1
Not Available	Completed	Treatment	Intra Operative Fluid Management	1
Not Available	Enrolling by Invitation	Not Available	Blood Transfusions / Catecholamine Treatment / Fetal Myocardial Function / Maternal Obesity During Childbirth / Medical Closere of Arterial Duct / Newborn Myocardial Function	1
Not Available	Recruiting	Basic Science	Health	1
Not Available	Recruiting	Treatment	Prolactinoma	1
Not Available	Recruiting	Treatment	Shock, Septic	1
Not Available	Unknown Status	Not Available	Parkinson's Disease (PD)	1
Not Available	Unknown Status	Treatment	Macroprolactinoma	1
Not Available	Unknown Status	Treatment	Arterial hypoxia	1

Pharmacoeconomics

Manufacturers

Abbott laboratories hosp products div
Abraxis pharmaceutical products
Astrazeneca lp
Baxter healthcare corp anesthesia and critical care
Hospira inc
International medication system
Luitpold pharmaceuticals inc
Smith and nephew solopak div smith and nephew
Teva parenteral medicines inc
Warner chilcott div warner lambert co
B braun medical inc
Baxter healthcare corp

Packagers

American Regent
B. Braun Melsungen AG
Baxter International Inc.
Bristol-Myers Squibb Co.
Cardinal Health
General Injectables and Vaccines Inc.
Hospira Inc.
Luitpold Pharmaceuticals Inc.
Physicians Total Care Inc.

Dosage forms

Form	Route	Strength
Injection, solution	Intravenous	160 mg/1mL
Injection, solution	Intravenous	40 mg/1mL
Injection, solution	Intravenous	80 mg/1mL
Solution	Intravenous
Liquid	Intravenous
Injection	Intravenous	40 mg/1mL
Injection	Intravenous	80 mg/1mL
Injection, solution, concentrate	Intravenous	40 mg/1mL
Injection, solution, concentrate	Intravenous	80 mg/1mL
Injection, solution	Intravenous	160 mg/100mL
Injection, solution	Intravenous	320 mg/100mL
Injection, solution	Intravenous	80 mg/100mL
Injection, solution	Intravenous
Injection, solution	Intravenous	0.8 mg/1mL
Injection, solution	Intravenous	1.6 mg/1mL
Injection, solution	Intravenous	3.2 mg/1mL
Solution	Intravenous
Injection	Intravenous

Prices

Unit description	Cost	Unit
Dopamine 40 mg/ml vial	0.15USD	ml
Dopamine 800 mg-d5w 500 ml	0.05USD	ml
Dopamine 400 mg-d5w 250 ml	0.04USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	128 °C	PhysProp
boiling point (°C)	227 °C at 2.30E+01 mm Hg	PhysProp
water solubility	600 g/L	Not Available
logP	-0.98	HANSCH,C ET AL. (1995)
Caco2 permeability	-5.03	ADME Research, USCD
pKa	8.93	PERRIN,DD (1965)

Predicted Properties

Property	Value	Source
Water Solubility	7.43 mg/mL	ALOGPS
logP	-0.4	ALOGPS
logP	0.03	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	10.01	ChemAxon
pKa (Strongest Basic)	9.27	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	66.48 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	43.25 m³·mol^-1	ChemAxon
Polarizability	16.21 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9547
Blood Brain Barrier	-	0.8414
Caco-2 permeable	-	0.5479
P-glycoprotein substrate	Non-substrate	0.5431
P-glycoprotein inhibitor I	Non-inhibitor	0.9739
P-glycoprotein inhibitor II	Non-inhibitor	0.9357
Renal organic cation transporter	Non-inhibitor	0.7115
CYP450 2C9 substrate	Non-substrate	0.8462
CYP450 2D6 substrate	Non-substrate	0.6383
CYP450 3A4 substrate	Non-substrate	0.6905
CYP450 1A2 substrate	Non-inhibitor	0.9046
CYP450 2C9 inhibitor	Non-inhibitor	0.9459
CYP450 2D6 inhibitor	Non-inhibitor	0.9422
CYP450 2C19 inhibitor	Non-inhibitor	0.9477
CYP450 3A4 inhibitor	Non-inhibitor	0.9001
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8648
Ames test	AMES toxic	0.9107
Carcinogenicity	Non-carcinogens	0.8642
Biodegradation	Ready biodegradable	0.7449
Rat acute toxicity	2.1415 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.7712
hERG inhibition (predictor II)	Non-inhibitor	0.5715

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	GC-MS	splash10-00di-1900000000-117a1a7207245f5377e7
GC-MS Spectrum - GC-MS (4 TMS)	GC-MS	splash10-00di-1900000000-8b7dcae82868308513da
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
GC-MS Spectrum - GC-EI-TOF	GC-MS	splash10-00di-1900000000-117a1a7207245f5377e7
GC-MS Spectrum - GC-MS	GC-MS	splash10-00di-1900000000-8b7dcae82868308513da
Mass Spectrum (Electron Ionization)	MS	splash10-00e9-8900000000-88acdc978fe4a64e0fc5
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	LC-MS/MS	splash10-0uxu-4900000000-ff51177ebcb89b8c956c
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	LC-MS/MS	splash10-0006-9200000000-a554eb700a06cecb8292
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	LC-MS/MS	splash10-014l-9000000000-db9813e1025f237a549b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	LC-MS/MS	splash10-0udi-0900000000-27e0d71db6d14d79759c
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	LC-MS/MS	splash10-0uk9-0900000000-f1cf97c0d0dd509e229e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	LC-MS/MS	splash10-00di-0900000000-aa09a2411e287abe74ed
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	LC-MS/MS	splash10-00di-1900000000-97c42b109cab2005373d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	LC-MS/MS	splash10-006x-9700000000-974bd18febffcceea2d6
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	LC-MS/MS	splash10-0f79-0900000000-099173d4201beca9e548
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	LC-MS/MS	splash10-000i-1900000000-9dc09f2661247c9d84b0
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	LC-MS/MS	splash10-0006-9300000000-8b85fa9aac1ffb4c2873
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	LC-MS/MS	splash10-0006-9000000000-9ea16d2057010279d433
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	LC-MS/MS	splash10-014l-9000000000-32ca2db8fe2b4729ab94
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	LC-MS/MS	splash10-0f79-0900000000-ff587935c79b4592ffcf
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	LC-MS/MS	splash10-000i-1900000000-8a35d8a2241bc18d6c50
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	LC-MS/MS	splash10-0006-9300000000-356a4b8f268863c7893e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	LC-MS/MS	splash10-0006-9000000000-a88c1004f357858fbc6c
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	LC-MS/MS	splash10-014l-9000000000-271874005dcb90288512
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-QFT , negative	LC-MS/MS	splash10-0udi-0900000000-cfa7e1cb9f02ffb4447d
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0udi-0900000000-46710e11fd65e4eff57b
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0fk9-0900000000-9dd18d949c0827d3f09e
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-00di-0900000000-7bc01b4577dd65504b1a
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-00di-0900000000-92056f2762508fb506f1
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-00di-0900000000-bd67f5e0746a2ca0a324
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash10-0udi-0900000000-27e0d71db6d14d79759c
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash10-0uk9-0900000000-f1cf97c0d0dd509e229e
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash10-00di-0900000000-501c6004e6d496b38d4f
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash10-00di-1900000000-97c42b109cab2005373d
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash10-006x-9700000000-974bd18febffcceea2d6
MS/MS Spectrum - Linear Ion Trap , negative	LC-MS/MS	splash10-00di-0900000000-c7eee50eadc1157e3f4e
MS/MS Spectrum - , negative	LC-MS/MS	splash10-0udi-0900000000-0975ff8173d3c9ccddd6
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-000i-0900000000-0a7d58ac6a4039fe88e3
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-000i-0900000000-b6a88ada58ee095efb64
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-000i-1900000000-6a41764b2a237d93a762
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-00ko-6900000000-572c1a8f1e8c0f7114ce
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0006-9300000000-148262aeb883ad1a8508
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0006-9100000000-bbb50786787764c3e72b
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0f79-0900000000-4769b29a6d00fe5d4db7
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-000i-1900000000-0827bb8aa6cc224fce1e
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0006-9300000000-3a862057cf8a009ef9bd
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0006-9000000000-fdcbbd6eae324ae068b8
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-014i-9000000000-76762d9949198fa094f7
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-0f79-0900000000-099173d4201beca9e548
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-000i-1900000000-9dc09f2661247c9d84b0
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-0006-9300000000-8b85fa9aac1ffb4c2873
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-0006-9000000000-9ea16d2057010279d433
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-014l-9000000000-32ca2db8fe2b4729ab94
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-0f79-0900000000-ff587935c79b4592ffcf
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-000i-1900000000-8a35d8a2241bc18d6c50
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-0006-9300000000-356a4b8f268863c7893e
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-0006-9000000000-a88c1004f357858fbc6c
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-014l-9000000000-271874005dcb90288512
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-000i-0900000000-ad06f0bcaccfb6ab447a
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-000i-0900000000-0bc64319c91c17ded449
MS/MS Spectrum - , positive	LC-MS/MS	splash10-000i-0900000000-8c08ab2bbc658f751898
1H NMR Spectrum	1D NMR	Not Applicable
[1H,13C] 2D NMR Spectrum	2D NMR	Not Applicable

Taxonomy

Description: This compound belongs to the class of organic compounds known as catecholamines and derivatives. These are compounds containing 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution.
Kingdom: Organic compounds
Super Class: Benzenoids
Class: Phenols
Sub Class: Benzenediols
Direct Parent: Catecholamines and derivatives
Alternative Parents: Phenethylamines / 2-arylethylamines / Aralkylamines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Organopnictogen compounds / Organooxygen compounds / Monoalkylamines / Hydrocarbon derivatives
Substituents: Catecholamine / Phenethylamine / 2-arylethylamine / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Aralkylamine / Monocyclic benzene moiety / Amine / Hydrocarbon derivative / Primary amine
Molecular Framework: Aromatic homomonocyclic compounds
External Descriptors: catecholamine (CHEBI:18243) / Biogenic amines, Tyramine derivatives, Dopamine (C03758)

Targets

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	170	N/A	N/A	7658429
EC 50 (nM)	18	N/A	N/A	15239663 / 17149874
EC 50 (nM)	209	N/A	N/A	18072730 / 18410082 / 19427222 / 20038106 / 20146482 / 20605099
EC 50 (nM)	227	N/A	N/A	22642365
EC 50 (nM)	43	N/A	N/A	18313303
EC 50 (nM)	65	N/A	N/A	23134120
EC 50 (nM)	8	N/A	N/A	17149874
IC 50 (nM)	0.000008	N/A	N/A	3156993
IC 50 (nM)	460	N/A	N/A	14592523
Ki (nM)	1.89	N/A	N/A	8893836 / 10465538
Ki (nM)	110	N/A	N/A	23428965
Ki (nM)	1100	N/A	N/A	10691700
Ki (nM)	15000	N/A	N/A	10691700
Ki (nM)	17	N/A	N/A	10691700
Ki (nM)	190	N/A	N/A	23428965
Ki (nM)	1900	N/A	N/A	10691700
Ki (nM)	2.9	N/A	N/A	20155917
Ki (nM)	20	N/A	N/A	10691700
Ki (nM)	2100	N/A	N/A	20155917 / 22846798
Ki (nM)	260	N/A	N/A	7658429
Ki (nM)	34	N/A	N/A	10691700
Ki (nM)	360	N/A	N/A	18834111
Ki (nM)	42	N/A	N/A	10691700
Ki (nM)	422	N/A	N/A	23134120
Ki (nM)	450	N/A	N/A	18834111
Ki (nM)	572	N/A	N/A	8893836
Ki (nM)	759	N/A	N/A	10465538
Ki (nM)	7940	N/A	N/A	9784114

Details1. Dopamine D2 receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: Potassium channel regulator activity
Specific Function: Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name: DRD2
Uniprot ID: P14416
Uniprot Name: D(2) dopamine receptor
Molecular Weight: 50618.91 Da

References

Ostadali MR, Ahangari G, Eslami MB, Razavi A, Zarrindast MR, Ahmadkhaniha HR, Boulhari J: The Detection of Dopamine Gene Receptors (DRD1-DRD5) Expression on Human Peripheral Blood Lymphocytes by Real Time PCR. Iran J Allergy Asthma Immunol. 2004 Dec;3(4):169-74. [PubMed:17301410]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	100	N/A	N/A	7658429
EC 50 (nM)	120	N/A	N/A	17154515
EC 50 (nM)	20	N/A	N/A	20709559
EC 50 (nM)	35	N/A	N/A	18313303
Kd (nM)	2500	N/A	N/A	8632409
Ki (nM)	>10000	N/A	N/A	1831904
Ki (nM)	12000	N/A	N/A	22846798
Ki (nM)	124	N/A	N/A	19454369
Ki (nM)	130	N/A	N/A	7658429
Ki (nM)	18200	N/A	N/A	9784114
Ki (nM)	192	N/A	N/A	1973733
Ki (nM)	2340	N/A	N/A	1826762
Ki (nM)	4470	N/A	N/A	9686407 / 23134120

Details2. Dopamine D1 receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: G-protein coupled amine receptor activity
Specific Function: Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name: DRD1
Uniprot ID: P21728
Uniprot Name: D(1A) dopamine receptor
Molecular Weight: 49292.765 Da

References

Ostadali MR, Ahangari G, Eslami MB, Razavi A, Zarrindast MR, Ahmadkhaniha HR, Boulhari J: The Detection of Dopamine Gene Receptors (DRD1-DRD5) Expression on Human Peripheral Blood Lymphocytes by Real Time PCR. Iran J Allergy Asthma Immunol. 2004 Dec;3(4):169-74. [PubMed:17301410]
Dolzan V, Plesnicar BK, Serretti A, Mandelli L, Zalar B, Koprivsek J, Breskvar K: Polymorphisms in dopamine receptor DRD1 and DRD2 genes and psychopathological and extrapyramidal symptoms in patients on long-term antipsychotic treatment. Am J Med Genet B Neuropsychiatr Genet. 2007 Sep 5;144B(6):809-15. [PubMed:17455212]
Hoenicka J, Aragues M, Ponce G, Rodriguez-Jimenez R, Jimenez-Arriero MA, Palomo T: From dopaminergic genes to psychiatric disorders. Neurotox Res. 2007 Jan;11(1):61-72. [PubMed:17449449]
da Silva Lobo DS, Vallada HP, Knight J, Martins SS, Tavares H, Gentil V, Kennedy JL: Dopamine genes and pathological gambling in discordant sib-pairs. J Gambl Stud. 2007 Dec;23(4):421-33. Epub 2007 Mar 30. [PubMed:17394052]
Fu W, Shen J, Luo X, Zhu W, Cheng J, Yu K, Briggs JM, Jin G, Chen K, Jiang H: Dopamine D1 receptor agonist and D2 receptor antagonist effects of the natural product (-)-stepholidine: molecular modeling and dynamics simulations. Biophys J. 2007 Sep 1;93(5):1431-41. Epub 2007 Apr 27. [PubMed:17468175]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	228	N/A	N/A	1826762
Ki (nM)	2440	N/A	N/A	15801855

Details3. Dopamine D5 receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: G-protein coupled amine receptor activity
Specific Function: Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Gene Name: DRD5
Uniprot ID: P21918
Uniprot Name: D(1B) dopamine receptor
Molecular Weight: 52950.5 Da

References

Ostadali MR, Ahangari G, Eslami MB, Razavi A, Zarrindast MR, Ahmadkhaniha HR, Boulhari J: The Detection of Dopamine Gene Receptors (DRD1-DRD5) Expression on Human Peripheral Blood Lymphocytes by Real Time PCR. Iran J Allergy Asthma Immunol. 2004 Dec;3(4):169-74. [PubMed:17301410]

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	4.76	N/A	N/A	20146482 / 20605099
EC 50 (nM)	6.1	N/A	N/A	23134120
EC 50 (nM)	8.53	N/A	N/A	18072730 / 18410082 / 19427222 / 20038106
EC 50 (nM)	8.57	N/A	N/A	22642365
Ki (nM)	13.2	N/A	N/A	8893836
Ki (nM)	15	N/A	N/A	22846798
Ki (nM)	1600	N/A	N/A	10691700
Ki (nM)	20	N/A	N/A	23134120
Ki (nM)	21	N/A	N/A	23428965
Ki (nM)	240	N/A	N/A	18834111
Ki (nM)	290	N/A	N/A	10691700
Ki (nM)	50	N/A	N/A	10691700
Ki (nM)	52	N/A	N/A	10691700
Ki (nM)	72	N/A	N/A	18834111

Details4. Dopamine D3 receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: G-protein coupled amine receptor activity
Specific Function: Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation.
Gene Name: DRD3
Uniprot ID: P35462
Uniprot Name: D(3) dopamine receptor
Molecular Weight: 44224.335 Da

References

Ostadali MR, Ahangari G, Eslami MB, Razavi A, Zarrindast MR, Ahmadkhaniha HR, Boulhari J: The Detection of Dopamine Gene Receptors (DRD1-DRD5) Expression on Human Peripheral Blood Lymphocytes by Real Time PCR. Iran J Allergy Asthma Immunol. 2004 Dec;3(4):169-74. [PubMed:17301410]

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	10	N/A	N/A	17154515
EC 50 (nM)	2.2	N/A	N/A	15239663 / 17149874
EC 50 (nM)	2.7	N/A	N/A	17149874
Ki (nM)	1.2	N/A	N/A	10691700
Ki (nM)	15	N/A	N/A	11206464
Ki (nM)	3310	N/A	N/A	15801855
Ki (nM)	57	N/A	N/A	10691700
Ki (nM)	6.2	N/A	N/A	18834111
Ki (nM)	62	N/A	N/A	10691700
Ki (nM)	97	N/A	N/A	10691700

Details5. Dopamine D4 receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: Sh3 domain binding
Specific Function: Dopamine receptor responsible for neuronal signaling in the mesolimbic system of the brain, an area of the brain that regulates emotion and complex behavior. Its activity is mediated by G proteins ...
Gene Name: DRD4
Uniprot ID: P21917
Uniprot Name: D(4) dopamine receptor
Molecular Weight: 48359.86 Da

References

Ostadali MR, Ahangari G, Eslami MB, Razavi A, Zarrindast MR, Ahmadkhaniha HR, Boulhari J: The Detection of Dopamine Gene Receptors (DRD1-DRD5) Expression on Human Peripheral Blood Lymphocytes by Real Time PCR. Iran J Allergy Asthma Immunol. 2004 Dec;3(4):169-74. [PubMed:17301410]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	1770	N/A	N/A	8302271
Ki (nM)	3100	N/A	N/A	8302271
Ki (nM)	5300	N/A	N/A	8302271
Ki (nM)	5900	N/A	N/A	8302271
Ki (nM)	6400	N/A	N/A	14592523
Ki (nM)	67	N/A	N/A	8302271

Details6. Sodium-dependent dopamine transporter

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inducer

General Function: Monoamine transmembrane transporter activity
Specific Function: Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name: SLC6A3
Uniprot ID: Q01959
Uniprot Name: Sodium-dependent dopamine transporter
Molecular Weight: 68494.255 Da

References

Ostadali MR, Ahangari G, Eslami MB, Razavi A, Zarrindast MR, Ahmadkhaniha HR, Boulhari J: The Detection of Dopamine Gene Receptors (DRD1-DRD5) Expression on Human Peripheral Blood Lymphocytes by Real Time PCR. Iran J Allergy Asthma Immunol. 2004 Dec;3(4):169-74. [PubMed:17301410]

Details7. Dopamine beta-hydroxylase

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Ligand

General Function: L-ascorbic acid binding
Specific Function: Conversion of dopamine to noradrenaline.
Gene Name: DBH
Uniprot ID: P09172
Uniprot Name: Dopamine beta-hydroxylase
Molecular Weight: 69064.45 Da

References

Goldman JM, Cooper RL, Murr AS: Reproductive functions and hypothalamic catecholamines in response to the soil fumigant metam sodium: adaptations to extended exposures. Neurotoxicol Teratol. 2007 May-Jun;29(3):368-76. Epub 2006 Dec 6. [PubMed:17258889]
Arboleda G, Huang TJ, Waters C, Verkhratsky A, Fernyhough P, Gibson RM: Insulin-like growth factor-1-dependent maintenance of neuronal metabolism through the phosphatidylinositol 3-kinase-Akt pathway is inhibited by C2-ceramide in CAD cells. Eur J Neurosci. 2007 May;25(10):3030-8. [PubMed:17561816]
Garland EM, Black BK, Harris PA, Robertson D: Dopamine-beta-hydroxylase in postural tachycardia syndrome. Am J Physiol Heart Circ Physiol. 2007 Jul;293(1):H684-90. [PubMed:17625104]
Pyatskowit JW, Prohaska JR: Rodent brain and heart catecholamine levels are altered by different models of copper deficiency. Comp Biochem Physiol C Toxicol Pharmacol. 2007 Mar;145(2):275-81. Epub 2007 Jan 12. [PubMed:17287146]
LeBlanc J, Ducharme MB: Plasma dopamine and noradrenaline variations in response to stress. Physiol Behav. 2007 Jun 8;91(2-3):208-11. Epub 2007 Mar 2. [PubMed:17433386]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	>30000	N/A	N/A	14592523
Ki (nM)	8248	N/A	N/A	9686407

Details8. 5-hydroxytryptamine receptor 1A

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General Function: Serotonin receptor activity
Specific Function: G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name: HTR1A
Uniprot ID: P08908
Uniprot Name: 5-hydroxytryptamine receptor 1A
Molecular Weight: 46106.335 Da

References

Weber JT, Hayataka K, O'Connor MF, Parker KK: Rabbit cerebral cortex 5HT1a receptors. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1997 May;117(1):19-24. [PubMed:9185324]
Toll L, Berzetei-Gurske IP, Polgar WE, Brandt SR, Adapa ID, Rodriguez L, Schwartz RW, Haggart D, O'Brien A, White A, Kennedy JM, Craymer K, Farrington L, Auh JS: Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications. NIDA Res Monogr. 1998 Mar;178:440-66. [PubMed:9686407]

Details9. 5-hydroxytryptamine receptor 7

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General Function: Serotonin receptor activity
Specific Function: This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor ...
Gene Name: HTR7
Uniprot ID: P34969
Uniprot Name: 5-hydroxytryptamine receptor 7
Molecular Weight: 53554.43 Da

References

Lovenberg TW, Baron BM, de Lecea L, Miller JD, Prosser RA, Rea MA, Foye PE, Racke M, Slone AL, Siegel BW, et al.: A novel adenylyl cyclase-activating serotonin receptor (5-HT7) implicated in the regulation of mammalian circadian rhythms. Neuron. 1993 Sep;11(3):449-58. [PubMed:8398139]
Shen Y, Monsma FJ Jr, Metcalf MA, Jose PA, Hamblin MW, Sibley DR: Molecular cloning and expression of a 5-hydroxytryptamine7 serotonin receptor subtype. J Biol Chem. 1993 Aug 25;268(24):18200-4. [PubMed:8394362]

Details10. D(1) dopamine receptor (Protein Group)

Kind: Protein group
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: G-protein coupled amine receptor activity
Specific Function: Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.

Components:

Name	UniProt ID
D(1A) dopamine receptor	P21728
D(1B) dopamine receptor	P21918

References

Hubner H, Haubmann C, Utz W, Gmeiner P: Conjugated enynes as nonaromatic catechol bioisosteres: synthesis, binding experiments, and computational studies of novel dopamine receptor agonists recognizing preferentially the D(3) subtype. J Med Chem. 2000 Feb 24;43(4):756-62. [PubMed:10691700]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	323	N/A	N/A	10411589

Details11. Sodium-dependent noradrenaline transporter

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

General Function: Norepinephrine:sodium symporter activity
Specific Function: Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name: SLC6A2
Uniprot ID: P23975
Uniprot Name: Sodium-dependent noradrenaline transporter
Molecular Weight: 69331.42 Da

References

Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, Partilla JS: Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin. Synapse. 2001 Jan;39(1):32-41. [PubMed:11071707]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	>1100000	N/A	N/A	14592523

Details12. Sodium-dependent serotonin transporter

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

General Function: Serotonin:sodium symporter activity
Specific Function: Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
Gene Name: SLC6A4
Uniprot ID: P31645
Uniprot Name: Sodium-dependent serotonin transporter
Molecular Weight: 70324.165 Da

References

Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, Partilla JS: Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin. Synapse. 2001 Jan;39(1):32-41. [PubMed:11071707]

Details13. 5-hydroxytryptamine receptor 3A

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Voltage-gated potassium channel activity
Specific Function: This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gate...
Gene Name: HTR3A
Uniprot ID: P46098
Uniprot Name: 5-hydroxytryptamine receptor 3A
Molecular Weight: 55279.835 Da

References

Rusch D, Musset B, Wulf H, Schuster A, Raines DE: Subunit-dependent modulation of the 5-hydroxytryptamine type 3 receptor open-close equilibrium by n-alcohols. J Pharmacol Exp Ther. 2007 Jun;321(3):1069-74. Epub 2007 Mar 7. [PubMed:17360702]

Details14. 5-hydroxytryptamine receptor 3B

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Serotonin-activated cation-selective channel activity
Specific Function: This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gate...
Gene Name: HTR3B
Uniprot ID: O95264
Uniprot Name: 5-hydroxytryptamine receptor 3B
Molecular Weight: 50291.3 Da

References

Rusch D, Musset B, Wulf H, Schuster A, Raines DE: Subunit-dependent modulation of the 5-hydroxytryptamine type 3 receptor open-close equilibrium by n-alcohols. J Pharmacol Exp Ther. 2007 Jun;321(3):1069-74. Epub 2007 Mar 7. [PubMed:17360702]

Details15. Superoxide dismutase [Cu-Zn]

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Zinc ion binding
Specific Function: Destroys radicals which are normally produced within the cells and which are toxic to biological systems.
Gene Name: SOD1
Uniprot ID: P00441
Uniprot Name: Superoxide dismutase [Cu-Zn]
Molecular Weight: 15935.685 Da

References

Wright GS, Antonyuk SV, Kershaw NM, Strange RW, Samar Hasnain S: Ligand binding and aggregation of pathogenic SOD1. Nat Commun. 2013;4:1758. doi: 10.1038/ncomms2750. [PubMed:23612299]

Details16. Synaptic vesicular amine transporter

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Monoamine transmembrane transporter activity
Specific Function: Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles...
Gene Name: SLC18A2
Uniprot ID: Q05940
Uniprot Name: Synaptic vesicular amine transporter
Molecular Weight: 55712.075 Da

References

Gonzalez AM, Walther D, Pazos A, Uhl GR: Synaptic vesicular monoamine transporter expression: distribution and pharmacologic profile. Brain Res Mol Brain Res. 1994 Mar;22(1-4):219-26. [PubMed:7912402]

Enzymes

Details1. Amine oxidase [flavin-containing] A

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Serotonin binding
Specific Function: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name: MAOA
Uniprot ID: P21397
Uniprot Name: Amine oxidase [flavin-containing] A
Molecular Weight: 59681.27 Da

References

Bortolato M, Chen K, Shih JC: Monoamine oxidase inactivation: from pathophysiology to therapeutics. Adv Drug Deliv Rev. 2008 Oct-Nov;60(13-14):1527-33. doi: 10.1016/j.addr.2008.06.002. Epub 2008 Jul 4. [PubMed:18652859]
Kaludercic N, Carpi A, Menabo R, Di Lisa F, Paolocci N: Monoamine oxidases (MAO) in the pathogenesis of heart failure and ischemia/reperfusion injury. Biochim Biophys Acta. 2011 Jul;1813(7):1323-32. doi: 10.1016/j.bbamcr.2010.09.010. Epub 2010 Sep 24. [PubMed:20869994]
Volavka J, Bilder R, Nolan K: Catecholamines and aggression: the role of COMT and MAO polymorphisms. Ann N Y Acad Sci. 2004 Dec;1036:393-8. [PubMed:15817751]

Details2. Amine oxidase [flavin-containing] B

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Primary amine oxidase activity
Specific Function: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name: MAOB
Uniprot ID: P27338
Uniprot Name: Amine oxidase [flavin-containing] B
Molecular Weight: 58762.475 Da

References

Bortolato M, Chen K, Shih JC: Monoamine oxidase inactivation: from pathophysiology to therapeutics. Adv Drug Deliv Rev. 2008 Oct-Nov;60(13-14):1527-33. doi: 10.1016/j.addr.2008.06.002. Epub 2008 Jul 4. [PubMed:18652859]
Kaludercic N, Carpi A, Menabo R, Di Lisa F, Paolocci N: Monoamine oxidases (MAO) in the pathogenesis of heart failure and ischemia/reperfusion injury. Biochim Biophys Acta. 2011 Jul;1813(7):1323-32. doi: 10.1016/j.bbamcr.2010.09.010. Epub 2010 Sep 24. [PubMed:20869994]

Details3. Catechol O-methyltransferase

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: O-methyltransferase activity
Specific Function: Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOP...
Gene Name: COMT
Uniprot ID: P21964
Uniprot Name: Catechol O-methyltransferase
Molecular Weight: 30036.77 Da

References

Ittiwut R, Listman JB, Ittiwut C, Cubells JF, Weiss RD, Brady K, Oslin D, Farrer LA, Kranzler HR, Gelernter J: Association between polymorphisms in catechol-O-methyltransferase (COMT) and cocaine-induced paranoia in European-American and African-American populations. Am J Med Genet B Neuropsychiatr Genet. 2011 Sep;156B(6):651-60. doi: 10.1002/ajmg.b.31205. Epub 2011 Jun 8. [PubMed:21656904]
Boot E, Booij J, Abeling N, Meijer J, da Silva Alves F, Zinkstok J, Baas F, Linszen D, van Amelsvoort T: Dopamine metabolism in adults with 22q11 deletion syndrome, with and without schizophrenia--relationship with COMT Val(1)(0)(8)/(1)(5)(8)Met polymorphism, gender and symptomatology. J Psychopharmacol. 2011 Jul;25(7):888-95. doi: 10.1177/0269881111400644. Epub 2011 Mar 29. [PubMed:21447540]
Volavka J, Bilder R, Nolan K: Catecholamines and aggression: the role of COMT and MAO polymorphisms. Ann N Y Acad Sci. 2004 Dec;1036:393-8. [PubMed:15817751]

Details4. Dopamine beta-hydroxylase

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: L-ascorbic acid binding
Specific Function: Conversion of dopamine to noradrenaline.
Gene Name: DBH
Uniprot ID: P09172
Uniprot Name: Dopamine beta-hydroxylase
Molecular Weight: 69064.45 Da

References

Goldman JM, Cooper RL, Murr AS: Reproductive functions and hypothalamic catecholamines in response to the soil fumigant metam sodium: adaptations to extended exposures. Neurotoxicol Teratol. 2007 May-Jun;29(3):368-76. Epub 2006 Dec 6. [PubMed:17258889]
Arboleda G, Huang TJ, Waters C, Verkhratsky A, Fernyhough P, Gibson RM: Insulin-like growth factor-1-dependent maintenance of neuronal metabolism through the phosphatidylinositol 3-kinase-Akt pathway is inhibited by C2-ceramide in CAD cells. Eur J Neurosci. 2007 May;25(10):3030-8. [PubMed:17561816]
Garland EM, Black BK, Harris PA, Robertson D: Dopamine-beta-hydroxylase in postural tachycardia syndrome. Am J Physiol Heart Circ Physiol. 2007 Jul;293(1):H684-90. [PubMed:17625104]
Pyatskowit JW, Prohaska JR: Rodent brain and heart catecholamine levels are altered by different models of copper deficiency. Comp Biochem Physiol C Toxicol Pharmacol. 2007 Mar;145(2):275-81. Epub 2007 Jan 12. [PubMed:17287146]
LeBlanc J, Ducharme MB: Plasma dopamine and noradrenaline variations in response to stress. Physiol Behav. 2007 Jun 8;91(2-3):208-11. Epub 2007 Mar 2. [PubMed:17433386]

Transporters

Details1. Solute carrier family 22 member 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Quaternary ammonium group transmembrane transporter activity
Specific Function: Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name: SLC22A2
Uniprot ID: O15244
Uniprot Name: Solute carrier family 22 member 2
Molecular Weight: 62579.99 Da

References

Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. [PubMed:12089365]
Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [PubMed:9830022]
Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759]
Busch AE, Karbach U, Miska D, Gorboulev V, Akhoundova A, Volk C, Arndt P, Ulzheimer JC, Sonders MS, Baumann C, Waldegger S, Lang F, Koepsell H: Human neurons express the polyspecific cation transporter hOCT2, which translocates monoamine neurotransmitters, amantadine, and memantine. Mol Pharmacol. 1998 Aug;54(2):342-52. [PubMed:9687576]
Grundemann D, Koster S, Kiefer N, Breidert T, Engelhardt M, Spitzenberger F, Obermuller N, Schomig E: Transport of monoamine transmitters by the organic cation transporter type 2, OCT2. J Biol Chem. 1998 Nov 20;273(47):30915-20. [PubMed:9812985]
Verhaagh S, Schweifer N, Barlow DP, Zwart R: Cloning of the mouse and human solute carrier 22a3 (Slc22a3/SLC22A3) identifies a conserved cluster of three organic cation transporters on mouse chromosome 17 and human 6q26-q27. Genomics. 1999 Jan 15;55(2):209-18. [PubMed:9933568]
Grundemann D, Liebich G, Kiefer N, Koster S, Schomig E: Selective substrates for non-neuronal monoamine transporters. Mol Pharmacol. 1999 Jul;56(1):1-10. [PubMed:10385678]

Details2. Solute carrier family 22 member 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Secondary active organic cation transmembrane transporter activity
Specific Function: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name: SLC22A1
Uniprot ID: O15245
Uniprot Name: Solute carrier family 22 member 1
Molecular Weight: 61153.345 Da

References

Bednarczyk D, Ekins S, Wikel JH, Wright SH: Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol. 2003 Mar;63(3):489-98. [PubMed:12606755]
Zhang L, Schaner ME, Giacomini KM: Functional characterization of an organic cation transporter (hOCT1) in a transiently transfected human cell line (HeLa). J Pharmacol Exp Ther. 1998 Jul;286(1):354-61. [PubMed:9655880]
Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759]
Busch AE, Quester S, Ulzheimer JC, Gorboulev V, Akhoundova A, Waldegger S, Lang F, Koepsell H: Monoamine neurotransmitter transport mediated by the polyspecific cation transporter rOCT1. FEBS Lett. 1996 Oct 21;395(2-3):153-6. [PubMed:8898084]
Breidert T, Spitzenberger F, Grundemann D, Schomig E: Catecholamine transport by the organic cation transporter type 1 (OCT1). Br J Pharmacol. 1998 Sep;125(1):218-24. [PubMed:9776363]
Boxberger KH, Hagenbuch B, Lampe JN: Common drugs inhibit human organic cation transporter 1 (OCT1)-mediated neurotransmitter uptake. Drug Metab Dispos. 2014 Jun;42(6):990-5. doi: 10.1124/dmd.113.055095. Epub 2014 Mar 31. [PubMed:24688079]
Grundemann D, Liebich G, Kiefer N, Koster S, Schomig E: Selective substrates for non-neuronal monoamine transporters. Mol Pharmacol. 1999 Jul;56(1):1-10. [PubMed:10385678]

Details3. Solute carrier family 22 member 3

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

General Function: Toxin transporter activity
Specific Function: Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name: SLC22A3
Uniprot ID: O75751
Uniprot Name: Solute carrier family 22 member 3
Molecular Weight: 61279.485 Da

References

Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [PubMed:9830022]

Details4. Solute carrier family 22 member 5

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

General Function: Symporter activity
Specific Function: Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name: SLC22A5
Uniprot ID: O76082
Uniprot Name: Solute carrier family 22 member 5
Molecular Weight: 62751.08 Da

References

Ohashi R, Tamai I, Nezu Ji J, Nikaido H, Hashimoto N, Oku A, Sai Y, Shimane M, Tsuji A: Molecular and physiological evidence for multifunctionality of carnitine/organic cation transporter OCTN2. Mol Pharmacol. 2001 Feb;59(2):358-66. [PubMed:11160873]
Wu X, Huang W, Prasad PD, Seth P, Rajan DP, Leibach FH, Chen J, Conway SJ, Ganapathy V: Functional characteristics and tissue distribution pattern of organic cation transporter 2 (OCTN2), an organic cation/carnitine transporter. J Pharmacol Exp Ther. 1999 Sep;290(3):1482-92. [PubMed:10454528]

Details5. POU domain, class 5, transcription factor 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Ubiquitin protein ligase binding
Specific Function: Transcription factor that binds to the octamer motif (5'-ATTTGCAT-3'). Forms a trimeric complex with SOX2 on DNA and controls the expression of a number of genes involved in embryonic development s...
Gene Name: POU5F1
Uniprot ID: Q01860
Uniprot Name: POU domain, class 5, transcription factor 1
Molecular Weight: 38570.415 Da

References

Zhu HJ, Appel DI, Grundemann D, Markowitz JS: Interaction of organic cation transporter 3 (SLC22A3) and amphetamine. J Neurochem. 2010 Jul;114(1):142-9. doi: 10.1111/j.1471-4159.2010.06738.x. Epub 2010 Apr 6. [PubMed:20402963]

Drug created on June 13, 2005 07:24 / Updated on February 26, 2020 21:39

Dopamine

Identification

Structure for Dopamine (DB00988)

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Properties

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Components:

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Enzymes

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Transporters

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