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 (1S,2R,4R)-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^[1]) is a non-selective, non-competitive antagonist of the nicotinic acetylcholine receptors (nAChRs) that was introduced in the 1950s as an antihypertensive drug.^[2] In the United States, it was voluntarily withdrawn from the market in 2009 but was brought to market in 2013 as Vecamyl and eventually was marketed by Turing Pharmaceuticals.^[3]^[4]

Chemically, mecamylamine is a secondary aliphatic amine, with a pK_aH of 11.2^[5]

^ "Mecamylamine". drugs.com. Retrieved May 15, 2015.
^ Bacher I, Wu B, Shytle DR, George TP (November 2009). "Mecamylamine - a nicotinic acetylcholine receptor antagonist with potential for the treatment of neuropsychiatric disorders". Expert Opinion on Pharmacotherapy. 10 (16): 2709–2721. doi:10.1517/14656560903329102. PMID 19874251. S2CID 25690407.
^ "Drug Profile: Mecamylamine - Targacept". AdisInsight. Springer Nature Switzerland AG.
^ "Drugs@FDA: FDA Approved Drug Products". www.accessdata.fda.gov. Retrieved 2017-10-16.
^ Schanker LS, Shore PA, Brodie BB, Hogben CA (August 1957). "Absorption of drugs from the stomach. I. The rat". The Journal of Pharmacology and Experimental Therapeutics. 120 (4): 528–539. PMID 13476377.