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Substance Name: Mecamylamine hydrochloride [USP]
RN: 826-39-1
UNII: 4956DJR58O
InChIKey: PKVZBNCYEICAQP-UHFFFAOYSA-N

Note

  • A nicotinic antagonist that is well absorbed from the gastrointestinal tract and crosses the blood-brain barrier. Mecamylamine has been used as a ganglionic blocker in treating hypertension, but, like most ganglionic blockers, is more often used now as a research tool.

Molecular Formula

  • C11-H21-N.Cl-H

Molecular Weight

  • 203.7548
 

Classification Codes

  • Antihypertensive
  • Antihypertensive Agents
  • Cholinergic Antagonists
  • Drug / Therapeutic Agent
  • Ganglionic Blockers
  • Neurotransmitter Agents
  • Nicotinic Antagonists
  • Peripheral Nervous System
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Names and Synonyms

Name of Substance

  • Mecamylamine hydrochloride [USP]

Synonyms

  • 3-Methylaminoisocamphane hydrochloride
  • 3-Methylaminoisokamfan chlorid
  • 3-Methylaminoisokamfan chlorid [Czech]
  • Bicyclo(2.2.1)heptan-2-amine, N,2,3,3-tetramethyl-, hydrochloride
  • CPDB 0059
  • EINECS 212-555-8
  • Inversine
  • Mecamine hydrochloride
  • Mecamylamine HCl
  • Mecamylamine hydrochloride
  • Mekamin hydrochloride
  • Mevasin
  • Mevasine
  • N,2,3,3-Tetramethyl-2-norbornanamine hydrochloride
  • N-Methyl-dl-isobornylamine hydrochloride
  • N-Methyl-N-2,5-endomethylene-1,6,6-trimethylcyclohexylamine hydrochloride
  • UNII-4956DJR58O
  • Vecamyl

Systematic Names

  • 2-Norbornanamine, N,2,3,3-tetramethyl-, hydrochloride
  • Bicyclo(2.2.1)heptan-2-amine, N,2,3,3-tetramethyl-, hydrochloride
  • Mecamylamine hydrochloride

Registry Numbers

CAS Registry Number

  • 826-39-1

FDA UNII

  • 4956DJR58O

System Generated Number

  • 0000826391

Molecular Formulas

Molecular Formula

  • C11-H21-N.Cl-H

Molecular Formula Fragments

  • C11-H21-N
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

1S/C11H21N.ClH/c1-10(2)8-5-6-9(7-8)11(10,3)12-4;/h8-9,12H,5-7H2,1-4H3;1H

InChIKey

PKVZBNCYEICAQP-UHFFFAOYSA-N

Smiles

CC1(C2CCC(C2)C1(C)NC)C.Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect 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.