Tripelennamine

Tripelennamine
Tripelennamine
Systematic (IUPAC) name
N',N'-dimethyl-N-(phenylmethyl)-N-pyridin-2-ylethane-1,2-diamine
Clinical data
AHFS/Drugs.com Multum Consumer Information
MedlinePlus a601044
Pregnancy cat.  ?
Legal status  ?
Routes Oral, Intravenous
Pharmacokinetic data
Metabolism Hepatic hydroxylation and glucuronidation
Excretion Renal
Identifiers
CAS number 91-81-6 YesY
154-69-8 (monohydrochloride)
22306-05-4 (hydrochloride)
57116-36-6 (maleate)
6138-56-3 (citrate)
ATC code D04AA04 R06AC04
PubChem CID 5587
DrugBank APRD00689
ChemSpider 5385 YesY
UNII 3C5ORO99TY YesY
KEGG D08645 YesY
ChEMBL CHEMBL1241 YesY
Chemical data
Formula C16H21N3 
Mol. mass 255.358 g/mol
SMILES eMolecules & PubChem
 YesY(what is this?)  (verify)

Tripelennamine (sold as Pyribenzamine by Novartis) is psychoactive drug and member of the pyridine and ethylenediamine chemical classes that is used as an antipruritic and first-generation antihistamine. It can be used in the treatment of asthma, hay fever, rhinitus and urticaria, but is now less common as it has been replaced by newer antihistamines.

Contents

History

Tripelennamine was first synthesized by Carl Djerassi, working in the laboratory of Charles Huttrer at Ciba, shortly after Djerassi got his B.S. It was his first patent.

Pharmacology

Tripelennamine functions primarily as an antihistamine, or H1 receptor antagonist. It is also mildly anticholinergic, or muscarinic acetylcholine receptor antagonistic. Notably, in addition to its antihistamine and anticholinergic effects, tripelennamine also functions as a weak serotonin reuptake inhibitor (SRI) and dopamine reuptake inhibitor (DRI).[1][2][3] Because of its SRI properties, tripelennamine was used as the basis for the development of the selective serotonin reuptake inhibitor (SSRI) fluvoxamine (Luvox).[4] In addition, due to its DRI properties, it is occasionally abused as a recreational drug (see below).

Side effects

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

Recreational use

Tripelennamine is sometimes abused recreationally in combination with the synthetic opioid pentazocine ("T's & Blues"),[5] or morphine ("Blue Velvet"), by preparing an injection containing both agents; tripelennamine is also used with cough syrups and analgesic solid preparations containing opioids including codeine, propoxyphene (Darvocet), dextropropoxyphene (Darvocet-N, Di-Gesic), hydrocodone (Vicodin, Xodol, Lortab), ethylmorphine (Dionine, codethyline), paregoric, benzylmorphine, tramadol (Ultram, Ultracet, Rybix, Tramal), oxycodone (Percocet, Roxicet, Tylox, OxyContin, OxyNorm), and dihydrocodeine and its derivatives. hydromorphone (Palladone, dilaudid), oxymorphone (Opana, Numorphan), and solid forms of methadone (Symoron, Pinadone) by either method.

It is dangerous to combine an opiate with a sedating antihistamine via injection, although the use of antihistamines (usually by mouth) to reduce opioid requirements for pain relief is a well-known practice, which is done under medical supervision with tripelennamine, as well as hydroxyzine, cyclizine, promethazine, diphenhydramine, phenindamine, orphenadrine, meclozine, chlorpheniramine, cyproheptadine and others; this method is doubly useful when used with opioids which release a great deal of histamine when administered and therefore cause itching, redness of skin and other histamine-related effects.

Like many of the first-generation antihistamines of the ethanolamine and alkylamine classes, tripelennamine and other members of its chemical class (ethylenediamines) produces a marginal to moderate euphoria; triepelennamine has a euphoriant effect with a relatively rapid onset and up to eight hours in duration. The ethylenediamine antihistamines rank between the ethanolamines and the alkylamines in this effect—somewhat weaker than orphenadrine and phenyltoloxamine, a bit stronger than brompheniramine and roughly comparable to dexchlorpheniramine and triprolidine.[citation needed]

An episode of Joe Frank's NPR radio show, Somewhere Out There, was devoted to Pyribenzamine and its recreational devotees.

Chemistry

Tripelennamine, N-benzyl-N′,N′-dimethyl-N-2-pyridylethylenediamine, is synthesized by reacting 2-benzylaminopyrridine with 2-dimethylaminoethylchloride in the presence of sodium amide. 2-Benzylaminopyrridine, in turn, can be easily synthesized by reduction of a Schiff base, synthesized by condensation of 2-aminopyrridine with benzaldehyde. Tripelennamine synthesis.png

References

  1. ^ Oishi R, Shishido S, Yamori M, Saeki K (February 1994). "Comparison of the effects of eleven histamine H1-receptor antagonists on monoamine turnover in the mouse brain". Naunyn-Schmiedeberg's Archives of Pharmacology 349 (2): 140–4. PMID 7513381. 
  2. ^ Sato T, Suemaru K, Matsunaga K, Hamaoka S, Gomita Y, Oishi R (May 1996). "Potentiation of L-dopa-induced behavioral excitement by histamine H1-receptor antagonists in mice". Japanese Journal of Pharmacology 71 (1): 81–4. doi:10.1254/jjp.71.81. PMID 8791174. http://joi.jlc.jst.go.jp/JST.Journalarchive/jphs1951/71.81?from=PubMed. [dead link]
  3. ^ Yeh SY, Dersch C, Rothman R, Cadet JL (September 1999). "Effects of antihistamines on 3, 4-methylenedioxymethamphetamine-induced depletion of serotonin in rats". Synapse 33 (3): 207–17. doi:10.1002/(SICI)1098-2396(19990901)33:3<207::AID-SYN5>3.0.CO;2-8. PMID 10420168. 
  4. ^ ), David Healy (MRC Psych (2004-01). Let them eat Prozac: the unhealthy ... - Google Books. ISBN 9780814736692. http://books.google.com/books?id=5w64WC_-jbMC&lpg=PP1&dq=let%20them%20eat%20prozac&pg=RA1-PA295. 
  5. ^ McGwier BW, Alpert MA, Panayiotou H, Lambert CR (June 1992). "Acute myocardial infarction associated with intravenous injection of pentazocine and tripelennamine". Chest 101 (6): 1730–2. doi:10.1378/chest.101.6.1730. PMID 1600804. 
v · d · eAntipruritics (D04)
Antihistamines for topical use
Anesthetics for topical use

M: INT, SF, LCT

anat/phys/devp

noco(i/b/d/q/u/r/p/m/k/v/f)/cong/tumr(n/e/d), sysi/epon

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Look at other dictionaries:

  • tripelennamine hydrochloride — An antihistamine. Also available, with the same actions, is t. citrate; it is less bitter than the hydrochloride salt, and is therefore used in elixir. * * * [USP] the monohydrochloride salt of tripelennamine, having the same actions and uses as… …   Medical dictionary

  • tripelennamine citrate — the citrate salt of tripelennamine, used as an antihistamine in the symptomatic treatment of allergic disorders, administered orally …   Medical dictionary

  • tripelennamine — /truy pe len euh meen , min/, n. Pharm. a white, crystalline, antihistamine, C16H21N3, used for the treatment of allergic disorders. [TRI + P(YRIDINE) + E(THY)LENE + (DI)AMINE] * * * …   Universalium

  • tripelennamine — noun A psychoactive drug of the pyridine and ethylenediamine classes, used as an antipruritic and first generation antihistamine …   Wiktionary

  • tripelennamine — tri·pel·en·na·mine .trī pe len ə .mēn, mən n an antihistamine drug derived from pyridine and ethylenediamine and used in the form of its crystalline citrate C16H21N3·C6H8O7 or hydrochloride C16H21N3·HCl see PYRIBENZAMINE * * * tri·pe·len·na·mine… …   Medical dictionary

  • tripelennamine — n. antihistamine medication used to treat allergies …   English contemporary dictionary

  • tripelennamine — tri·pel·en·na·mine …   English syllables

  • tripelennamine — ˌtrīˌpeˈlenəˌmēn, mə̇n noun ( s) Etymology: tri + pyridine + ethylenediamine : an antihistamine drug C16H21N3 derived from pyridine and ethylenediamine and used in the form of its crystalline citrate or hydrochloride …   Useful english dictionary

  • Diphenhydramine — Systematic (IUPAC) name 2 (diphenylmethoxy) N,N dimethylethanamine Clinical data Trade names Benadryl …   Wikipedia

  • Phenothiazine — Phenothiazine …   Wikipedia

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