Pethidine intermediate A

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Pethidine intermediate A
Pethidineintermediate.svg
Clinical data
Routes of
administration 		N/A
ATC code
  • none
Legal status
Legal status
Identifiers
  • 1-methyl-4-phenylpiperidine-4-carbonitrile
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.020.771 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C13H16N2
Molar mass 200.285 g·mol−1
3D model (JSmol)
  • CN1CCC(CC1)(C#N)c2ccccc2
  • InChI=1S/C13H16N2/c1-15-9-7-13(11-14,8-10-15)12-5-3-2-4-6-12/h2-6H,7-10H2,1H3
  • Key:ZLFQTZYFXYOGLS-UHFFFAOYSA-N
   (verify)

Pethidine intermediate A is a 4-phenyl piperidine derivative that is a precursor to the opioid analgesic drug pethidine (meperidine). It is not known to have any analgesic activity in its own right, however other derivatives of pethidine with a 4-cyano group in place of the carboxylate ethyl ester have been found to be active, [1] so pethidine intermediate A might also show opioid effects. It is scheduled by UN Single Convention on Narcotic Drugs. It is a Schedule II Narcotic controlled substance in the United States and has an ACSCN of 9232. The 2014 annual manufacturing quota was 6 grammes (as an end product, presumably for research use). [2]

See also

Related Research Articles

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<span class="mw-page-title-main">Desmethylprodine</span> Chemical compound

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<span class="mw-page-title-main">Pethidine</span> Opioid analgesic

Pethidine, also known as meperidine and sold under the brand name Demerol among others, is a synthetic opioid pain medication of the phenylpiperidine class. Synthesized in 1938 as a potential anticholinergic agent by the German chemist Otto Eisleb, its analgesic properties were first recognized by Otto Schaumann while working for IG Farben, Germany. Pethidine is the prototype of a large family of analgesics including the pethidine 4-phenylpiperidines, the prodines, bemidones and others more distant, including diphenoxylate and analogues.

<span class="mw-page-title-main">Phenoperidine</span> Chemical compound

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<span class="mw-page-title-main">Properidine</span> Chemical compound

Properidine is an opioid, an analgesic, and the isopropyl analog of pethidine. Properidine is under international control and is listed in the United States under the Controlled Substances Act (1970) as a Schedule I substance. It is a narcotic, with an Administrative Controlled Substances Code Number (ACSCN) of 9644 and a 2 gramme annual aggregate manufacturing quota as of 2014. The salt in use is hydrochloride, with a free base conversion ratio of 0.88.

<span class="mw-page-title-main">Hydroxypethidine</span> Chemical compound

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<span class="mw-page-title-main">Allylprodine</span> Chemical compound

Allylprodine is an opioid analgesic that is an analog of prodine. It was discovered by Hoffman-La Roche in 1957 during research into the related drug pethidine. Derivatives were tested to prove the theory that phenolic & non-phenolic opioids bind at different sites of the opiate receptor.

<span class="mw-page-title-main">Meprodine</span> Chemical compound

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<span class="mw-page-title-main">Propiram</span> Chemical compound

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<span class="mw-page-title-main">Ethoheptazine</span> Chemical compound

Ethoheptazine is an opioid analgesic from the phenazepane family. It was invented in the 1950s and is a ring expanded analogue of pethidine.

<span class="mw-page-title-main">Norpethidine</span> Chemical compound

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<span class="mw-page-title-main">Pethidinic acid</span> Chemical compound

Pethidinic acid is a 4-phenylpiperidine derivative that is both a metabolite of and a precursor to pethidine (meperidine). It is scheduled by UN Single Convention on Narcotic Drugs. It is a Schedule II Narcotic controlled substance in the United States and has an ACSCN of 9234. The 2014 annual manufacturing quota was 6 grams.

<span class="mw-page-title-main">Benzethidine</span> Chemical compound

Benzethidine is a 4-phenylpiperidine derivative that is related to the clinically used opioid analgesic drug pethidine.

<span class="mw-page-title-main">Etoxeridine</span> Chemical compound

Etoxeridine is a 4-phenylpiperidine derivative that is related to the clinically used opioid analgesic drug pethidine (meperidine).

<span class="mw-page-title-main">Furethidine</span> Chemical compound

Furethidine is a 4-phenylpiperidine derivative that is related to the clinically used opioid analgesic drug pethidine (meperidine), but with around 25x higher potency. According to another source, Furethidine is 500/30 = 16.7 x the potency of pethidine.

<span class="mw-page-title-main">Morpheridine</span> Chemical compound

Morpheridine (Morpholinoethylnorpethidine) is a 4-phenylpiperidine derivative that is related to the clinically used opioid analgesic drug pethidine (meperidine). It is a strong analgesic with around 4 times the potency of pethidine, and unlike pethidine, does not cause convulsions, although it produces the standard opioid side effects such as sedation and respiratory depression.

<span class="mw-page-title-main">Pheneridine</span> Chemical compound

Pheneridine is a 4-Phenylpiperidine derivative that is related to the opioid analgesic drug pethidine (meperidine).

<span class="mw-page-title-main">Oxpheneridine</span> Chemical compound

Oxpheneridine is a 4-phenylpiperidine derivative that is related to the opioid analgesic drug pethidine (meperidine).

<span class="mw-page-title-main">Picenadol</span> Chemical compound

Picenadol (LY-97435) is a 4-phenylpiperidine derivative that is an opioid analgesic drug developed by Eli Lilly in the 1970s.

<span class="mw-page-title-main">4-Fluoropethidine</span> Chemical compound

4-Fluoropethidine is a drug that is a derivative of pethidine (meperidine), which combines pethidine's opioid analgesic effects with increased monoamine reuptake inhibition. It is around 50% less potent than pethidine as an opioid analgesic, but conversely is 50% more potent as a dopamine reuptake inhibitor, with other derivatives such as the 4-iodo and 3,4-dichloro analogues being even more potent dopamine reuptake inhibitors again. However none of these compounds substitute for cocaine or produce stimulant effects in animals, suggesting that they still act primarily as opioid analgesic drugs in practice. Its action and degree of relation to pethidine means that it may be controlled in those countries which have laws about controlled-substance analogues; it is not itself listed in the Controlled Substances Act 1970.

References

  1. ↑ Lomenzo SA, Rhoden JB, Izenwasser S, Wade D, Kopajtic T, Katz JL, Trudell ML (March 2005). "Synthesis and biological evaluation of meperidine analogues at monoamine transporters". Journal of Medicinal Chemistry. 48 (5): 1336–43. doi:10.1021/jm0401614. PMID   15743177.
  2. ↑ "Conversion Factors for Controlled Substances". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice.
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