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Phenindamine

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Chemical compound
Pharmaceutical compound
Phenindamine
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Identifiers
  • 2-methyl-9-phenyl-2,3,4,9-tetrahydro-1H-indeno[2,1-c]pyridine
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Chemical and physical data
FormulaC19H19N
Molar mass261.368 g·mol−1
3D model (JSmol)
  • CN(C1)CCC2=C1C(C3=C2C=CC=C3)C4=CC=CC=C4
  • 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 ☒N
  • Key:ISFHAYSTHMVOJR-UHFFFAOYSA-N ☒N
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Phenindamine (Nolahist,Thephorin) is anantihistamine andanticholinergic closely related tocyproheptadine. It was developed byHoffman-La Roche in the late 1940s.[1] It is used to treat symptoms of thecommon cold andallergies, such as sneezing, itching, rashes, andhives. Its efficacy against some symptoms of opioid withdrawal was researched in the 1950s and 1960s in a number of countries;William S. Burroughs' bookJunkie 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 byValeant, 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 exhibitoptical isomerism as do other chemicals of its general type ranging frompethidine andalphaprodine tocyproheptadine.[2]

See also

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References

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