Structure via PubChem · Public domain (PubChem)
mecamylamine
Sign in to saveMecamylamine (INN, BAN; or mecamylamine hydrochloride (USAN); brand names Inversine, Vecamyl) is a non-selective, non-competitive antagonist of the nicotinic acetylcholine receptors (nAChRs) that was introduced in the 1950s as an antihypertensive drug. In the United States, it was voluntarily withdrawn from the market in 2009 but was brought to market in 2013 as Vecamyl and eventually was marketed by Turing Pharmaceuticals.
Chemical data
- Formula
- C11H21N
- Molecular weight
- 167.29 g/mol
- IUPAC name
- N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine
- SMILES
- CC1(C2CCC(C2)C1(C)NC)C
- InChIKey
- IMYZQPCYWPFTAG-UHFFFAOYSA-N
- XLogP
- 2.6
- Polar surface area
- 12 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1956
- Admin. routes
- oral
- Indications
- hypertension, age-related macular degeneration, nicotine dependence, macular degeneration
via ChEMBL · EBI
Research
3,488 papers- Mecamylamine: new therapeutic uses and toxicity/risk profile.Clinical therapeutics · 2001
- Mecamylamine (a nicotine antagonist) for smoking cessation.The Cochrane database of systematic reviews · 2000
- Nicotine-mecamylamine interactions.Clinical pharmacology and therapeutics · 2000
- Mecamylamine - a nicotinic acetylcholine receptor antagonist with potential for the treatment of neuropsychiatric disorders.Expert opinion on pharmacotherapy · 2009
- Mecamylamine (Inversine): an old antihypertensive with new research directions.Journal of human hypertension · 2002
via PubMed
Wikidata facts
- Mass
- 167.1674
Show 6 more facts
- Commons category
- Mecamylamine
- World Health Organisation international non-proprietary name
- mecamylamine
- chemical formula
- C₁₁H₂₁N
- medical condition treated
- arterial hypertension
- canonical SMILES
- CC1(C2CCC(C2)C1(C)NC)C
- subject has role
- nicotinic antagonist
via Wikidata · CC0
~3 min read
Encyclopedic overview
6 sectionsContents
- Medical uses
- Overdose
- Pharmacology
- History
- See also
- References
Mecamylamine (INN, BAN; or mecamylamine hydrochloride (USAN); brand names Inversine, Vecamyl) is a non-selective, non-competitive antagonist of the nicotinic acetylcholine receptors (nAChRs) that was introduced in the 1950s as an antihypertensive drug. In the United States, it was voluntarily withdrawn from the market in 2009 but was brought to market in 2013 as Vecamyl and eventually was marketed by Turing Pharmaceuticals.
Chemically, mecamylamine is a secondary aliphatic amine, with a pKaH of 11.2
Excerpted from Wikipedia’s “mecamylamine” article, available under the CC BY-SA 4.0 licence.