PEPAP

PEPAP
PEPAP
Systematic (IUPAC) name
4-phenyl-1-(2-phenylethyl)piperidin-4-yl acetate
Clinical data
Pregnancy cat.  ?
Legal status  ? (UK) Schedule I (US)
Identifiers
CAS number 64-52-8
ATC code  ?
PubChem CID 60977
DrugBank DB01562
ChemSpider 54939 YesY
Synonyms PEPAP
Chemical data
Formula C21H25NO2 
Mol. mass 323.43 g/mol
SMILES eMolecules & PubChem
 YesY(what is this?)  (verify)

PEPAP is an opioid analgesic that is an analog of pethidine (meperidine).

It is related to the drug MPPP, with an N-phenethyl group in place of the N-methyl substitution and an acetate ester rather than propionate. PEPAP is approximately 6-7 times more potent than morphine in laboratory rats.[1] PEPAP presumably has similar effects to other opioids, producing analgesia, sedation and euphoria. Side effects can include itching, nausea and potentially serious respiratory depression which can be life-threatening.

PEPAP has been found to be a potent CYP2D6 inhibitor, which makes it likely to cause adverse interactions with some other drugs, although the inhibitory potency of PEPAP is less than that of MPPP.[2] (Both cocaine and methadone are also CYP2D6 inhibitors and could, in theory, potentiate the effect.)

It is unlikely that the tetrahydropyridine byproducts that may be formed during the synthesis of PEPAP are neurotoxic in the same way as the MPPP byproduct MPTP. It appears that the N-methyl group of MPTP is required for neurotoxic activity. In animal experiments, only MPTP analogues that preserved the N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine structure were active as dopaminergic neurotoxins. Most structural changes, including replacing the N-methyl group with other substituents, abolished neurotoxicity.[3]

There is evidence that the clandestine manufacturers who produced MPPP in the 1970s (included the tainted batch) went on to produce PEPAP[4] in an attempt to avoid using watched precursors or drug intermediates that were illegal.

References

  1. ^ Janssen, PA; Eddy, NB (1960). "Compounds related to pethidine-IV. New general chemical methods of increasing the analgesic activity of pethidine". Journal of medicinal and pharmaceutical chemistry 2: 31–45. doi:10.1021/jm50008a003. PMID 14406754. 
  2. ^ Pritzker, D; Kanungo, A; Kilicarslan, T; Tyndale, RF; Sellers, EM (2002). "Designer drugs that are potent inhibitors of CYP2D6". Journal of clinical psychopharmacology 22 (3): 330–2. PMID 12006905. 
  3. ^ Youngster, SK; Sonsalla, PK; Sieber, BA; Heikkila, RE (1989). "Structure-activity study of the mechanism of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced neurotoxicity. I. Evaluation of the biological activity of MPTP analogs". The Journal of pharmacology and experimental therapeutics 249 (3): 820–8. PMID 2786564. 
  4. ^ The Case of the Frozen Addicts (ISBN 0-679-42465-2)

Wikimedia Foundation. 2010.

Игры ⚽ Нужна курсовая?

Look at other dictionaries:

  • Opioid — Endogenous opioid peptides Skeletal molecular images Adrenorphin Amidorphin Casomorphin …   Wikipedia

  • Convention Unique Sur Les Stupéfiants De 1961 — La convention unique sur les stupéfiants de 1961 convoquée par l ONU fut ratifiée le 30 mars 1961 à New York. Elle comporte 183 signataires au 1er novembre 2005, elle est entrée en vigueur en 1964 et fut modifiée par le protocole du 25 mars… …   Wikipédia en Français

  • Convention unique sur les stupefiants de 1961 — Convention unique sur les stupéfiants de 1961 La convention unique sur les stupéfiants de 1961 convoquée par l ONU fut ratifiée le 30 mars 1961 à New York. Elle comporte 183 signataires au 1er novembre 2005, elle est entrée en vigueur en… …   Wikipédia en Français

  • Convention unique sur les stupéfiants de 1961 — La convention unique sur les stupéfiants de 1961 convoquée par l ONU fut ratifiée le 30 mars 1961 à New York. Elle comporte 183 signataires au 1er novembre 2005, elle est entrée en vigueur en 1964 et fut modifiée par le protocole du 25 mars… …   Wikipédia en Français

  • Morphine — This article is about the drug. For other meanings, see Morphine (disambiguation). Morphia redirects here. For other uses, see Morphia (disambiguation). Not to be confused with Morphinae, Morphea, or Morpholine. Morphine …   Wikipedia

  • Opiate — For other uses see Opiate (disambiguation), or for the class of drugs see Opioid. Harvesting the poppy pod. In medicine, the term opiate describes any of the narcotic opioid alkaloids found as natural products in the opium poppy plant …   Wikipedia

  • Phencyclidine — Systematic (IUPAC) name …   Wikipedia

  • Loperamide — Imodium redirects here. For the song by Nirvana, see Breed (song). Loperamide Systematic (IUPAC) name …   Wikipedia

  • Pethidine — Systematic (IUPAC) name …   Wikipedia

  • Opioid receptor — Opioid receptors are a group of G protein coupled receptors with opioids as ligands.[1][2][3] The endogenous opioids are dynorphins, enkephalins, endorphins, endomorphins and nociceptin. The opioid receptors are 40% identical to somatostatin… …   Wikipedia

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”