Phenindamine
Verifiedfieldschanged
Watchedfieldschanged
Verifiedrevid437157797
Iupac name2-methyl-9-phenyl-2,3,4,9-tetrahydro-1H-indeno[2,1-c]pyridine
Pregnancy usN
Legal usOTC
Cas number82-88-2
Atc prefixR06
Atc suffixAX04
Pubchem11291
DrugbankDB01619
Chemspiderid10817
Unii772BQ8KSST
KeggD08353
Chembl278398
C19
H19
N1
SmilesCN(C1)CCC2=C1C(C3=C2C=CC=C3)C4=CC=CC=C4
Stdinchi1S/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
StdinchikeyISFHAYSTHMVOJR-UHFFFAOYSA-N

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.[medical citation needed]

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.[2]

See also

References

  1. ^ "Pyridindenes and process for their manufacture". No. 2546652.
  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