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Substance Name: Mecamylamine [INN:BAN]
RN: 60-40-2
InChIKey: IMYZQPCYWPFTAG-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

Molecular Weight

  • 167.2939
 

Classification Codes

  • Antihypertensive Agents
  • Autonomic Agents
  • Cardiovascular Agents
  • Cholinergic Agents
  • Cholinergic Antagonists
  • Drug / Therapeutic Agent
  • Ganglionic Blockers
  • Neurotransmitter Agents
  • Nicotinic Antagonists
  • Peripheral Nervous System Agents

Names and Synonyms

Name of Substance

  • Mecamylamine
  • Mecamylamine [INN:BAN]

MeSH Heading

  • Mecamylamine

Synonyms

  • 2-Methylamino-2,3,3-trimethylnorbornane
  • 2-Methylaminoisocamphane
  • 3-beta-Methylamino-2,2,3-trimethylbicyclo(2.2.1)heptane
  • 3-Methylaminoisocamphane
  • 3-Methylaminoisokamfan
  • 3-Methylaminoisokamfan [Czech]
  • EINECS 200-476-1
  • Mecamilamina
  • Mecamilamina [DCIT]
  • Mecamilamina [Italian]
  • Mecamine
  • Mecamylamine
  • Mecamylaminum
  • Mecamylaminum [INN-Latin]
  • Mekamine
  • Mevasine
  • N,2,3,3-Tetramethyl-2-norbornamine
  • N,2,3,3-Tetramethyl-2-norcamphanamine
  • N-Methyl-2-isocamphanamine
  • Revertina
  • Versamine

Systematic Names

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

Registry Numbers

CAS Registry Number

  • 60-40-2

System Generated Number

  • 0000060402

Structure Descriptors

InChI

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

InChIKey

IMYZQPCYWPFTAG-UHFFFAOYSA-N

Smiles

CNC1(C)C2CCC(C2)C1(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 40mg/kg (40mg/kg) BEHAVIORAL: SLEEP Archivum Immunologiae et Therapiae Experimentalis. Vol. 10, Pg. 905, 1962.
mouse LD50 intravenous 11900ug/kg (11.9mg/kg)   United States Patent Document. Vol. #4168308,
mouse LD50 oral 90mg/kg (90mg/kg)   Bollettino Chimico Farmaceutico. Vol. 103, Pg. 490, 1964.
mouse LD50 subcutaneous 37500ug/kg (37.5mg/kg)   Farmakologiya i Toksikologiya Vol. 25, Pg. 163, 1962.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point < 25 deg C   EXP
log P (octanol-water) 3.310 (none)   EST
Atmospheric OH Rate Constant 7.01E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.