Piritramide

Overview

Piritramide (R-3365, trade names Dipidolor, Piridolan, Pirium and others) is a synthetic opioid analgesic (narcotic painkiller) that is marketed in certain European countries including: Austria, Belgium, Czech Republic, Slovenia, Germany and the Netherlands. It comes in free form, is about 0.75x times as potent as morphine and is given parenterally (by injection) for the treatment of severe pain. Nausea, vomiting, respiratory depression and constipation are believed to be less frequent with piritramide than with morphine (the gold standard opioid against which other opioids are compared and contrasted), and it produces more rapid-onset analgesia (pain relief) when compared to morphine and pethidine. After intravenous administration the onset of analgesia is as little as 1–2 minutes, which may be related to its great lipophilicity. The analgesic and sedative effects of piritramide are believed to be potentiated with phenothiazines and its emetic (nausea/vomiting-inducing) effects are suppressed. The volume of distribution is 0.7-1 L/kg after a single dose, 4.7-6 L/kg after steady-state concentrations are achieved and up to 11.1 L/kg after prolonged dosing.[1–4] WP

Piritramide was developed and patented in Belgium, at Janssen, in 1960. It is part of an eponymous two-member class of opioids in clinical use with the other being bezitramide (Burgodin). The closest chemical and structural relatives of piritramide in clinical use include the diphenoxylate family, fentanyl (both Janssen discoveries) and somewhat more distantly alphaprodine. WP

Not being in clinical use in the United States, it is a Schedule I Narcotic controlled substance with a DEA ACSCN of 9642 and manufacturing quota of zero.[5] WP

Chemistry

Formula

C27H34N4O PC

CAS number

302-41-0 PC

Molar mass (g/mol)

430.6 PC

IUPAC name (computed by PubChem)

1-(3-cyano-3,3-diphenylpropyl)-4-piperidin-1-ylpiperidine-4-carboxamide PC

SMILES

C1CCN(CC1)C2(CCN(CC2)CCC(C#N)(C3=CC=CC=C3)C4=CC=CC=C4)C(=O)N PC

InChIKey

IHEHEFLXQFOQJO-UHFFFAOYSA-N PC

PubChem CID

9331

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other US Patent 3080366
2. Other Piritramide. 23 September 2011
3. Journal / agency Kay B. A clinical investigation of piritramide in the treatment of postoperative pain. British Journal of Anaesthesia. December 1971. doi:10.1093/bja/43.12.1167 · PMID 4945251
4. Other FACHINFORMATION (Zusammenfassung der Merkmale des Arzneimittels). November 2013
5. Other DEA Diversion Control Division

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