Prodine

Source: Wikipedia, the free encyclopedia.
Prodine
Skeletal formula of prodine
Ball-and-stick model of the prodine molecule
Clinical data
ATC code
  • none
Legal status
Legal status
  • AU: S8 (Controlled drug)
  • BR: Class A1 (Narcotic drugs)[1]
  • DE: Anlage I (Authorized scientific use only)
  • US: Schedule I
  • In general: ℞ (Prescription only)
Identifiers
  • (1,3-Dimethyl-4-phenylpiperidin-4-yl) propanoate
JSmol)
  • O=C(CC)O[C@]1(CCN(C[C@H]1C)C)C2=CC=CC=C2
  • InChI=1S/C16H23NO2/c1-4-15(18)19-16(14-8-6-5-7-9-14)10-11-17(3)12-13(16)2/h5-9,13H,4,10-12H2,1-3H3/t13-,16+/m1/s1 checkY
  • Key:UVAZQQHAVMNMHE-CJNGLKHVSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Prodine[2] (trade names Prisilidine and Nisentil) is an opioid analgesic that is an analog of pethidine (meperidine). It was developed in Germany in the late 1940s.

There are two

racemates.[3] Alphaprodine is closely related to desomorphine in steric configuration.[3] The cis form also has active isomers but none are used in medicine.[3][4] Betaprodine is around five times more potent than alphaprodine[5] but is metabolized more rapidly, and only alphaprodine was developed for medicinal use. It has similar activity to pethidine, but with a more rapid onset and shorter duration of effects.[6] Betaprodine produces more euphoria and side effects than alphaprodine at all dose levels, and it was found that 5 to 10 mg of betaprodine is equivalent to 25 to 40 mg of alphaprodine.[3]

Testing in rats showed alphaprodine to be 97% the strength of

dextrorotatory cis isomer was 790% stronger.[3] Betaprodine taken orally was 420% stronger than oral methadone, the cis form was 390% stronger for the laevorotatory and 505% stronger for the dextrorotatory isomers.[3]

Alphaprodine was sold under several brand names, mainly Nisentil and Prisilidine. It was most commonly used for pain relief during childbirth[7] and dentistry,[8] as well as for some minor surgical procedures. Alphaprodine has a duration of action of 1 to 2 hours, and 40 to 60 mg is equivalent to 10 mg of subcutaneous morphine.

Prodine has broadly similar effects to other opioids, producing

respiratory depression which can lead to life-threatening respiratory arrest. Respiratory depression can be a problem with alphaprodine even at normal therapeutic doses.[9] Unlike pethidine, prodine does not produce toxic metabolites and is therefore more suitable for high-dose therapy.[medical citation needed
]

Regulation

Alphaprodine has a DEA ACSCN of 9010 and 2013 manufacturing quota of 3 grams; betaprodine has an ACSCN of 9611 and a 2 grams quota.

See also

References

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ US Patent 2498433 '1,3 dimethyl-4-propionoxy-4-phenyl-piperidine and acid addition salts thereof'
  3. ^
    OCLC 1628783
    .
  4. S2CID 46012276
    .
  5. ISBN 978-0-485-11171-2
    .
  6. S2CID 35046059
    .
  7. PMID 5907367
    .
  8. PMID 5221807
    .
  9. PMID 3560080
    .
Retrieved from "https://en.wikipedia.org/w/index.php?title=Prodine&oldid=1213930225"