Tripelennamine

Overview

Tripelennamine, sold under the brand name Pyribenzamine by Novartis, is a drug that is used as an antipruritic and first-generation antihistamine. It can be used in the treatment of asthma, hay fever, rhinitis, and urticaria, but is now less common as it has been replaced by newer antihistamines. The drug was patented at CIBA, which merged with Geigy into Ciba-Geigy, and eventually becoming Novartis. WP

Uses, dosage and effects

Medical uses

Where and when it is/was in common use, tripelennamine is used much like other mildly-anticholinergic antihistamines to treat conditions of the upper respiratory tract arising from illnesses and hay fever. It can be used alone or in combination with other agents to have the desired effect. Cough medicines of the general formula tripelennamine + codeine/dihydrocodine/hydrocodone ± expectorant ± decongestant(s) are popular where available. Among these are the Pyribenzamine cough syrups which contain codeine, with and without decongestants, listed in the 1978 Physicians' Desk Reference; the codeine-tripelennamine synergy is well-known and makes such mixtures more useful for their intended purposes. WP

Risks and side effects

Side effects

Tripelennamine is mildly sedating. Other side effects can include irritation, dry mouth, nausea, and dizziness. WP

Pharmacology

Pharmacodynamics

Tripelennamine acts primarily as an antihistamine, or H₁ receptor antagonist. It has little to no anticholinergic activity, with 180-fold selectivity for the H₁ receptor over the muscarinic acetylcholine receptors (for comparison, diphenhydramine had 20-fold selectivity for the H₁ receptor). In addition to its antihistamine properties, tripelennamine also acts as a weak serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI).[1–4] WP

Pharmacokinetics

The elimination half-life of tripelennamine is 4 to 6 hours. In a clinical study, the half-life of tripelennamine following intramuscular injection of 50 to 100 mg was 2.9 to 4.4 hours.[5][6][7] WP

History

History

Tripelennamine was patented in 1946 by Carl Djerassi and colleagues, working at CIBA in New Jersey.[8] WP

Legal status

Availability

Tripelennamine is available in the United States under the brand name PBZ OTC.[9] WP

Chemistry

Formula

C16H21N3 PC

CAS number

91-81-6 PC

Molar mass (g/mol)

255.36 PC

IUPAC name (computed by PubChem)

N'-benzyl-N,N-dimethyl-N'-pyridin-2-ylethane-1,2-diamine PC

SMILES

CN(C)CCN(CC1=CC=CC=C1)C2=CC=CC=N2 PC

InChIKey

UFLGIAIHIAPJJC-UHFFFAOYSA-N PC

PubChem CID

5587

IUPAC name

N,N-dimethyl-N'-(phenylmethyl)-N'-pyridin-2-ylethane-1,2-diamine WP

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. Journal / agency Kubo N, Shirakawa O, Kuno T, Tanaka C. Antimuscarinic effects of antihistamines: quantitative evaluation by receptor-binding assay. Jpn J Pharmacol. March 1987. doi:10.1254/jjp.43.277 · PMID 2884340
2. Journal / agency Oishi R, Shishido S, Yamori M, Saeki K. Comparison of the effects of eleven histamine H1-receptor antagonists on monoamine turnover in the mouse brain. Naunyn-Schmiedeberg's Archives of Pharmacology. February 1994. doi:10.1007/bf00169830 · PMID 7513381
3. Journal / agency Sato T, Suemaru K, Matsunaga K, Hamaoka S, Gomita Y, Oishi R. Potentiation of L-dopa-induced behavioral excitement by histamine H1-receptor antagonists in mice. Japanese Journal of Pharmacology. May 1996. doi:10.1254/jjp.71.81 · PMID 8791174
4. Journal / agency Yeh SY, Dersch C, Rothman R, Cadet JL. Effects of antihistamines on 3, 4-methylenedioxymethamphetamine-induced depletion of serotonin in rats. Synapse. September 1999. doi:10.1002/(SICI)1098-2396(19990901)33:3<207::AID-SYN5>3.0.CO;2-8 · PMID 10420168
5. Other Goldfrank LR, Flomenbaum N. Goldfrank's toxicologic emergencies. 2006
6. Journal / agency Yeh SY, Todd GD, Johnson RE, Gorodetzky CW, Lange WR. The pharmacokinetics of pentazocine and tripelennamine. Clin Pharmacol Ther. June 1986. doi:10.1038/clpt.1986.117 · PMID 3709032
7. Journal / agency Sharma A, Hamelin BA. Classic histamine H1 receptor antagonists: a critical review of their metabolic and pharmacokinetic fate from a bird's eye view. Curr Drug Metab. April 2003. doi:10.2174/1389200033489523 · PMID 12678691
8. Other Landau R, Achilladelis B, Scriabine A. Pharmaceutical Innovation: Revolutionizing Human Health. 1999
9. Other PBZ OTC

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