Name: Mecamylamine hydrochloride
SKU: 826-39-1

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Basic Information

Molecular Structure:
CAS No.:	826-39-1
Name:	Mecamylamine hydrochloride

Formula:	C₁₁H₂₁N^.HCl
Molecular Weight:	203.79
Synonyms:	2-Norbornanamine,N,2,3,3-tetramethyl-, hydrochloride (8CI);Bicyclo[2.2.1]heptan-2-amine,N,2,3,3-tetramethyl-, hydrochloride (9CI);CPDD 0059;Inversine;Mecamylaminechloride;Mevasin;Mevasine;N,2,3,3-Tetramethyl-2-norbornanamine hydrochloride;
EINECS:	212-555-8
Melting Point:	>240 °C (dec.)
Boiling Point:	189.3 °C at 760 mmHg
Flash Point:	58.1 °C
Solubility:	ethanol: 122 mg/mL
Appearance:	white solid
Hazard Symbols:	Xn
Risk Codes:	22-36/37/38
Safety:	36/37/39
Transport Information:	UN 2811 6.1/PG 3
PSA:	12.03000
LogP:	3.61350

Synthetic route

: 826-39-1
(+/-)-exo-mecamylamine hydrochloride

: 14649-03-7
(S)-phenylethyl isocyanate

A: (1S,2R,4R)-N-<((S)-1-phenylethyl)carbamoyl>mecamylamine

B: 107485-87-0
(1R,2R,4S)-N-<((S)-1-phenylethyl)carbamoyl>mecamylamine

Conditions

Conditions	Yield
With sodium carbonate 2.) CHCl3, 1 h, room t.; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 74-96-4
ethyl bromide

: 826-39-1
(+/-)-exo-mecamylamine hydrochloride

: N-ethyl mecamylamine

Conditions

Conditions	Yield
With potassium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide Alkylation; Heating;

: 826-39-1
(+/-)-exo-mecamylamine hydrochloride

: 100-44-7
benzyl chloride

: N-benzyl mecamylamine

Conditions

Conditions	Yield
With potassium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide Alkylation; Heating;

: 826-39-1
(+/-)-exo-mecamylamine hydrochloride

: 7051-34-5
cyclopropylcarbinyl bromide

: N-cyclopropylmethyl mecamylamine

Conditions

Conditions	Yield
With potassium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide Alkylation; Heating;

: 826-39-1
(+/-)-exo-mecamylamine hydrochloride

: 106-95-6
allyl bromide

: N-allyl mecamylamine

Conditions

Conditions	Yield
With potassium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide Alkylation; Heating;

: 826-39-1
(+/-)-exo-mecamylamine hydrochloride

: 106-96-7
propargyl bromide

: N-propargyl mecamylamine

Conditions

Conditions	Yield
With potassium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide Alkylation; Heating;

: 826-39-1
(+/-)-exo-mecamylamine hydrochloride

: 352-11-4
1-chloromethyl-4-fluorobenzene

: N-(4-fluorobenzyl) mecamylamine

Conditions

Conditions	Yield
With potassium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide Alkylation; Heating;

: 826-39-1
(+/-)-exo-mecamylamine hydrochloride

: 100-11-8
1-bromomethyl-4-nitro-benzene

: N-(4-nitrobenzyl) mecamylamine

Conditions

Conditions	Yield
With potassium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide Alkylation; Heating;

: 826-39-1
(+/-)-exo-mecamylamine hydrochloride

: S-(+)-mecamylamine hydrochloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) aq. Na2CO3 / 2.) CHCl3, 1 h, room t. 2: 64 percent / ethanol / 0.75 h / Heating View Scheme

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Chemistry

Chemistry informtion about Mevasin Hydrochloride (CAS NO.826-39-1) is:
IUPAC Name: N,5,6,6-Tetramethylbicyclo[2.2.1]Heptan-5-Amine Hydrochloride
Synonyms: N,2,3,3-Tetramethylbicyclo[2.2.1]Heptan-2-Amine Hydrochloride ; Inversine ; Mecamylamine ; Mecamylamine Hydrochloride ; 2-[Methylamino]Isocamphane Hydrochloride ; 3-Methylaminoisocamphanehydrochloride ; 3-Methylaminoisokamfanchlorid ; Inversinehydrochloride
Product Categories: Acetylcholine receptor
MF: C₁₁H₂₂ClN
MW: 203.75
EINECS: 212-555-8
Flash Point: 58.1 °C
Boiling Point: 189.3 °C at 760 mmHg
Vapour Pressure: 0.573 mmHg at 25°C
Enthalpy of Vaporization: 42.55 kJ/mol
Solubility ethanol: 122 mg/mL
Following is the molecular structure of Mevasin Hydrochloride (CAS NO.826-39-1) is:

Uses

Mevasin Hydrochloride (CAS NO.826-39-1) has been used as a ganglionic blocker in treating hypertension, but, like most ganglionic blockers, is more often used now as a research tool. It is also sometimes used as an anti-addictive drug to help people stop smoking tobacco, and is now more widely used for this application than it is for lowering blood pressure. This effect is thought to be due to it blocking α3β4 nicotinic receptors in the brain.

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
guinea pig	LD50	intraperitoneal	63mg/kg (63mg/kg)	Journal of Pharmacology and Experimental Therapeutics. Vol. 117, Pg. 169, 1956.
guinea pig	LD50	oral	175mg/kg (175mg/kg)	Journal of Pharmacology and Experimental Therapeutics. Vol. 117, Pg. 169, 1956.
guinea pig	LD50	subcutaneous	155mg/kg (155mg/kg)	Journal of Pharmacology and Experimental Therapeutics. Vol. 117, Pg. 169, 1956.
mouse	LD50	intraperitoneal	17mg/kg (17mg/kg)	Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 300, 1970.
mouse	LD50	intravenous	14mg/kg (14mg/kg)	Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 300, 1970.
mouse	LD50	oral	92mg/kg (92mg/kg)	Drugs in Japan Vol. 6, Pg. 814, 1982.
mouse	LD50	subcutaneous	81mg/kg (81mg/kg)	Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 300, 1970.
rat	LD50	intraperitoneal	53mg/kg (53mg/kg)	Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 301, 1970.
rat	LD50	intravenous	21mg/kg (21mg/kg)	Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 300, 1970.
rat	LD50	oral	208mg/kg (208mg/kg)	Journal of Pharmacology and Experimental Therapeutics. Vol. 117, Pg. 169, 1956.
rat	LD50	subcutaneous	177mg/kg (177mg/kg)	Journal of Pharmacology and Experimental Therapeutics. Vol. 117, Pg. 169, 1956.

Safety Profile

Poison by ingestion, intraperitoneal, intravenous, and subcutaneous routes. When heated to decomposition it emits very toxic fumes of HCl and NO_x.
Hazard Codes:
Harmful Xn
Risk Statements:
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements:
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: RB6900000

Specification

Biochem/physiol actions is Noncompetitive nicotinic acetylcholine receptor antagonist; preferentially blocks nicotinic receptors at autonomic ganglia; crosses blood-brain barrier. Caution solutions are stable to autoclaving.