Phenindamine

Phenindamine
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
ATC code	R06AX04 (WHO) ;
Legal status
Legal status	US: OTC;
Identifiers
	IUPAC name 2-methyl-9-phenyl-2,3,4,9-tetrahydro-1H-indeno[2,1-c]pyridine;
CAS Number	82-88-2 ;
PubChem CID	11291;
DrugBank	DB01619 ;
ChemSpider	10817 ;
UNII	772BQ8KSST;
KEGG	D08353 ;
ChEMBL	ChEMBL278398 ;
CompTox Dashboard (EPA)	DTXSID0023452 ;
ECHA InfoCard	100.001.313
Chemical and physical data
Formula	C19H19N
Molar mass	261.368 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(C1)CCC2=C1C(C3=C2C=CC=C3)C4=CC=CC=C4;
	InChI InChI=1S/C19H19N/c1-20-12-11-16-15-9-5-6-10-17(15)19(18(16)13-20)14-7-3-2-4-8-14/h2-10,19H,11-13H2,1H3 ; Key:ISFHAYSTHMVOJR-UHFFFAOYSA-N ;
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Phenindamine (Nolahist, Thephorin) is an antihistamine and anticholinergic closely related to cyproheptadine. It was developed by Hoffman-La Roche in the late 1940s.^[1] It is used to treat symptoms of the common cold and allergies, such as sneezing, itching, rashes, and hives. Its efficacy against some symptoms of opioid withdrawal was researched in the 1950s and 1960s in a number of countries; William S. Burroughs' book Junkie mentions this technique. Like many other first-generation antihistamines, phenindamine has useful potentiating effects on many narcotic analgesics and is even more useful with those opioids which release histamine when in the body.

Nolahist was originally manufactured in the US by Carnrick Laboratories, and later by Amarin Pharmaceuticals. When that company ceased its American operations, its product line was acquired by Valeant, but they declined to resume manufacturing Nolahist. The last produced lot bore an expiration date of 10/2005, and the product is no longer available.

Phenindamine does exhibit optical isomerism as do other chemicals of its general type ranging from pethidine and alphaprodine to cyproheptadine to certain herbicides and other industrial chemicals; the.^[2] In the example at hand, the compound isophenidamine (60295-96-7 MSDS), which is inactive.^[2]

References

^ US 2546652, Plati JT , Wenner W, "Pyridindenes and process for their manufacture", assigned to F Hoffmann La Roche AG
^ ^a ^b Tscherne RJ, Umagat H (March 1980). "Determination of isophenindamine in phenindamine tartrate using an argentated high-performance liquid chromatographic mobile phase". Journal of Pharmaceutical Sciences. 69 (3): 342–4. doi:10.1002/jps.2600690324. PMID 7381716.

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[1] US 2546652, Plati JT , Wenner W, "Pyridindenes and process for their manufacture", assigned to F Hoffmann La Roche AG

[jpharmsci-2] Tscherne RJ, Umagat H (March 1980). "Determination of isophenindamine in phenindamine tartrate using an argentated high-performance liquid chromatographic mobile phase". Journal of Pharmaceutical Sciences. 69 (3): 342–4. doi:10.1002/jps.2600690324. PMID 7381716.

[1]

Phenindamine

See also

References