Mecamylamine

Mecamylamine
Clinical data
Trade names	Inversine, Vecamyl
AHFS/Drugs.com	Consumer Drug Information
Routes of; administration	Oral
ATC code	C02BB01 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Protein binding	40%
Identifiers
	IUPAC name N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine;
CAS Number	6147-18-8 ;
PubChem CID	4032;
IUPHAR/BPS	3990;
DrugBank	DB00657 ;
ChemSpider	5036243 ;
UNII	6EE945D3OK;
KEGG	C07511;
ChEMBL	ChEMBL1398031 ;
CompTox Dashboard (EPA)	DTXSID0023240 ;
ECHA InfoCard	100.000.433
Chemical and physical data
Formula	C11H21N
Molar mass	167.296 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES N([C@@]2([C@@H]1CC[C@@H](C1)C2(C)C)C)C;
	InChI 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 ; Key:IMYZQPCYWPFTAG-IQJOONFLSA-N ;
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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 In the United States, it was voluntarily withdrawn from the market in 2009 but was brought to market in 2013 as Vecamyl and eventually was marketed by Turing Pharmaceuticals.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 pK_aH of 11.2