MECAMYLAMINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C11H21N
Molecular Weight	167.2911
Optical Activity	( + / - )
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN[C@@]1(C)[C@@H]2CC[C@@H](C2)C1(C)C

InChI

InChIKey=IMYZQPCYWPFTAG-NGZCFLSTSA-N

InChI=1S/C11H21N/c1-10(2)8-5-6-9(7-8)11(10,3)12-4/h8-9,12H,5-7H2,1-4H3/t8-,9+,11-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C11H21N
Molecular Weight	167.2911
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugs.com/cdi/mecamylamine.html | https://www.ncbi.nlm.nih.gov/pubmed/12080428 | https://www.ncbi.nlm.nih.gov/pubmed/23603417 | https://www.ncbi.nlm.nih.gov/pubmed/19874251

Mecamylamine (Inversine), the first orally available antihypertensive agent, is now rarely used. Introduced as a therapeutic agent for the treatment of hypertension in the 1950s, mecamylamine was the first useful ganglionic blocking agent that was not a quarternary ammonium compound. Mecamylamine is indicated for the management of moderately severe to severe essential hypertension and in uncomplicated cases of malignant hypertension. Mecamylamine reduces blood pressure in both normotensive and hypertensive individuals. A small oral dosage often produces a smooth and predictable reduction of blood pressure. Although this antihypertensive effect is predominantly orthostatic, the supine blood pressure is also significantly reduced. Mecamylamine is a nicotinic parasympathetic ganglionic blocker. Mecamylamine administration produces several deleterious side-effects at therapeutically relevant doses. As such, mecamylamine’s use as an antihypertensive agent was phased out, except in severe hypertension. Mecamylamine easily traverses the blood-brain barrier to reach the central nervous system (CNS), where it acts as a nicotinic acetylcholine receptor (nAChR) antagonist, inhibiting all known nAChR subtypes. Since nAChRs play a major role in numerous physiological and pathological processes, it is not surprising that mecamylamine has been evaluated for its potential therapeutic effects in a wide variety of CNS disorders, including addiction.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Neuronal acetylcholine receptor; alpha3/beta4 40 Target ID: CHEMBL1907594 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=e1fc95fe-7816-47b6-b73d-b2f644f79872&type=display \| https://www.ncbi.nlm.nih.gov/pubmed/19874251 \| https://www.ncbi.nlm.nih.gov/pubmed/11303054	Antagonist 2849		0.6 µM [Ki]
Neuronal acetylcholine receptor; alpha4/beta2 77 Target ID: CHEMBL1907589 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11303054	Antagonist 2849		2.5 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575 Sources: https://www.drugs.com/cdi/mecamylamine.html	Primary		Approved 8583	INVERSINE Approved Use For the management of moderately severe to severe essential hypertension and in uncomplicated cases of malignant hypertension. Launch Date 1956
Alcohol addiction 24 Sources: https://clinicaltrials.gov/ct2/show/NCT00563797	Primary		Phase III 665	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
7.89 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11354389	2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered:		MECAMYLAMINE HYDROCHLORIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
23.68 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11354389	7.5 mg single, oral dose: 7.5 mg route of administration: Oral experiment type: SINGLE co-administered:		MECAMYLAMINE HYDROCHLORIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
115.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11354389	2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered:	MECAMYLAMINE HYDROCHLORIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
149.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11354389	2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered:	MECAMYLAMINE HYDROCHLORIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
150.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11354389	2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered:	MECAMYLAMINE HYDROCHLORIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
352.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11354389	7.5 mg single, oral dose: 7.5 mg route of administration: Oral experiment type: SINGLE co-administered:	MECAMYLAMINE HYDROCHLORIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
467.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11354389	7.5 mg single, oral dose: 7.5 mg route of administration: Oral experiment type: SINGLE co-administered:	MECAMYLAMINE HYDROCHLORIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
472.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11354389	7.5 mg single, oral dose: 7.5 mg route of administration: Oral experiment type: SINGLE co-administered:	MECAMYLAMINE HYDROCHLORIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
10.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11354389	2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered:		MECAMYLAMINE HYDROCHLORIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
10.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11354389	7.5 mg single, oral dose: 7.5 mg route of administration: Oral experiment type: SINGLE co-administered:		MECAMYLAMINE HYDROCHLORIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
		CYP1A1 151

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A1 272	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/10594335/	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY34256
001 Chemical	DY34257
Alinda	ALBB-023410
Alinda	IBS-L0034437
BioSynth	Q-201341
BOC Sciences	107538-05-6
Chemspace	CSC015645827
Chemspace	CSC015659858
Compound Cloud	12358971
Compound Cloud	12358972
eMolecules	43050930
eMolecules	46011392
Enamine	BBV-77631107
Enamine	BBV-77652981
Hangzhou Yuhao Chemical Technology	RT3984
Lan Pharmatech	LQT-B47398
Molcore	MC34256
Molcore	MC34257
Toronto Research Chemicals	M202595
ZINC	ZINC000043763856	http://zinc15.docking.org/substances/ZINC000043763856

PubMed

Title	Date	PubMed
Prenatal nicotinic exposure upregulates pulmonary C-fiber NK1R expression to prolong pulmonary C-fiber-mediated apneic response.	2016-01-01	26524655
The effects of nicotine and tobacco particulate matter on dopamine uptake in the rat brain.	2014-02	23999947
Gestational exposure of mice to secondhand cigarette smoke causes bronchopulmonary dysplasia blocked by the nicotinic receptor antagonist mecamylamine.	2013-08	23757602
Discovery of isoxazole analogues of sazetidine-A as selective α4β2-nicotinic acetylcholine receptor partial agonists for the treatment of depression.	2011-10-27	21905669
Neurotoxicity induced by okadaic acid in the human neuroblastoma SH-SY5Y line can be differentially prevented by α7 and β2* nicotinic stimulation.	2011-09	21715663
Association of the histidine-triad nucleotide-binding protein-1 (HINT1) gene variants with nicotine dependence.	2011-08	20514075
Ryanodine receptor-2 upregulation and nicotine-mediated plasticity.	2011-01-05	21113126
ACSL6 is associated with the number of cigarettes smoked and its expression is altered by chronic nicotine exposure.	2011	22205969
Repetitive nicotine exposure leads to a more malignant and metastasis-prone phenotype of SCLC: a molecular insight into the importance of quitting smoking during treatment.	2010-08	20457658
Nicotinic receptor-mediated reduction in L-DOPA-induced dyskinesias may occur via desensitization.	2010-06	20200117
Activation and inhibition of mouse muscle and neuronal nicotinic acetylcholine receptors expressed in Xenopus oocytes.	2010-05	20100906
Neuronal nicotinic acetylcholine receptors as pharmacotherapeutic targets for the treatment of alcohol use disorders.	2010-03	20201817
The limbic circuitry underlying cocaine seeking encompasses the PPTg/LDT.	2009-10	19788581
Effects of mecamylamine on nicotine-induced conditioned hyperactivity and sensitization in differentially reared rats.	2009-07	19379770
Nicotine anxiogenic and rewarding effects are decreased in mice lacking beta-endorphin.	2009-06	19376143
Corticotropin-releasing factor within the central nucleus of the amygdala and the nucleus accumbens shell mediates the negative affective state of nicotine withdrawal in rats.	2009-06	19145226
Cardiovascular effect of peripheral injected melittin in normotensive conscious rats: Mediation of the central cholinergic system.	2009-04-14	19910175
Enhanced nicotine sensitivity in nociceptin/orphanin FQ receptor knockout mice.	2009-04	19371589
Distinct effects of nociceptin analogs on scopolamine-induced memory impairment in mice.	2009-01-14	19059236
Protective effects of mecamylamine and atropine against α(4)β(2) nicotinic receptor expression and functional toxicity in paraoxon-treated rats.	2008-09	21791372
Nicotinic signaling ameliorates acute bladder inflammation induced by protamine sulfate or cyclophosphamide.	2008-06	18433785
Receptor-mediated tobacco toxicity: acceleration of sequential expression of alpha5 and alpha7 nicotinic receptor subunits in oral keratinocytes exposed to cigarette smoke.	2008-05	18450646
Involvement of dorsal hippocampal nicotinic receptors in the effect of morphine on memory retrieval in passive avoidance task.	2008-04-28	18316071
Glutamatergic contributions to nicotinic acetylcholine receptor agonist-evoked cholinergic transients in the prefrontal cortex.	2008-04-02	18385335
Differential role of nicotinic acetylcholine receptor subunits in physical and affective nicotine withdrawal signs.	2008-04	18184829
Mecamylamine prevents neuronal apoptosis induced by glutamate and low potassium via differential anticholinergic-independent mechanisms.	2008-03	18222492
Nicotine-induced dystonic arousal complex in a mouse line harboring a human autosomal-dominant nocturnal frontal lobe epilepsy mutation.	2007-09-19	17881519
The involvement of the central cholinergic system in the pressor and bradycardic effects of centrally administrated melittin in normotensive conscious rats.	2007-04	17222905
Nicotinic modulation of gene expression in SH-SY5Y neuroblastoma cells.	2006-10-20	16949557
The nicotinic receptor antagonists abolish pathobiologic effects of tobacco-derived nitrosamines on BEP2D cells.	2006-10	16835749
Nicotine attenuates beta-amyloid-induced neurotoxicity by regulating metal homeostasis.	2006-06	16627626
Nicotine prevents experimental parkinsonism in rodents and induces striatal increase of neurotrophic factors.	1998-12	9832142
Anti-nicotinic properties of anticholinergic antiparkinson drugs.	1998-11	9877318
Rat alpha3/beta4 subtype of neuronal nicotinic acetylcholine receptor stably expressed in a transfected cell line: pharmacology of ligand binding and function.	1998-08	9687574
[Assessment of anti-tremorogenic drugs--nicotine-induced tail-tremor model].	1997-06	9278937
Role of central nicotinic and beta-adrenergic receptors in the onset and further development of tail-tremor induced by repeated nicotine administration to rats.	1997-05	9151294
[3H]benzylpempidine, a new radioligand for probing a putative channel site on nicotinic cholinergic receptors.	1997	9096244
Tacrine interacts with an allosteric activator site on alpha 4 beta 2 nAChRs in M10 cells.	1996-09-02	8930989
5HT3 receptor antagonists do not block nicotine induced hyperactivity in rats.	1995-05	7659769
The role of brain acetylcholine in phenol-induced tremor in mice.	1995-05	7639639
Characteristics of tail-tremor induced by nicotine in rats.	1994-08	7990972
Nicotine-sensitive paresis.	1992-02	1736170
Evidence for an involvement of D1 and D2 dopamine receptors in mediating nicotine-induced hyperactivity in rats.	1991	1833784
Nicotine-induced tail-tremor and drug effects.	1989-12	2576144
The effect of cholinergic stimulation in the nucleus accumbens on locomotor behavior.	1988-02-16	3359231
Mecamylamine blockade of nicotine responses: evidence for two brain nicotinic receptors.	1986-06	3737641
Neuropharmacology of the parasitic trematode, Schistosoma mansoni.	1983-01	6130710
Pharmacokinetics of nicotine in adult and infant mice.	1977-12	599971
Effect of cholingeric drugs on methadone-induced catalepsy and stereotypies in rats treated chronically with methadone.	1976-10	987911
Effects of ganglion blocking agents on nicotine extensor convulsions and lethality in mice.	1969-09	4390479

Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dose for Hypertension 2.5 mg orally twice a day; may increase by one 2.5 mg tablet at intervals of 2 days or more until desired blood pressure response is achieved. Comments: -The average total daily dose is 25 mg, usually in 3 divided doses; however, 2.5 mg daily may be sufficient. Partial tolerance may develop in certain patients, which requires an increase in the total daily dose. -Four or more doses may be required when smooth control is difficult to obtain. -Titration should be determined by blood pressure readings in the erect position at the time of maximal effect of this drug, as well as by signs and symptoms of orthostatic hypotension. In severe or urgent cases, titration at larger increments and shorter intervals may be needed.

Route of Administration: Oral

In Vitro Use Guide

10 uM of either mecamylamine stereoisomer produced significant inhibition of the nAChR subtypes.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:59:09 GMT 2025` Edited by `admin` on `Wed Apr 02 08:59:09 GMT 2025`
Record UNII	6EE945D3OK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MECAMYLAMINE

Official Name

English

MECAMYLAMINE [MI]

Preferred Name

English

mecamylamine [INN]

Common Name

English

BICYCLO(2.2.1)HEPTAN-2-AMINE, N,2,3,3-TETRAMETHYL-

Systematic Name

English

MECAMYLAMINE [VANDF]

Common Name

English

Mecamylamine [WHO-DD]

Common Name

English

N,2,3,3-TETRAMETHYL-2-NORBORNANAMINE

Systematic Name

English

(1RS,2SR,4SR)-N,2,3,3-TETRAMETHYLBICYCLO(2.2.1)HEPTAN-2-AMINE

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

C02BB01