Tripelennamine

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Tripelennamine
Systematic (IUPAC) name
N-benzyl-N',N'-dimethyl-N- pyridin-2-yl-ethane-1,2-diamine
Identifiers
CAS number	91-81-6 154-69-8 (monohydrochloride) 22306-05-4 (hydrochloride) 57116-36-6 (maleate) 6138-56-3 (citrate)
ATC code	D04AA04 R06AC04
PubChem	5587
DrugBank	APRD00689
Chemical data
Formula	C16H21N3
Mol. mass	255.358 g/mol
Pharmacokinetic data
Bioavailability	?
Metabolism	Hepatic hydroxylation and glucuronidation
Half life	?
Excretion	Renal
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

Tripelennamine (INN, also known as pyribenzamine) is a first generation pyridine antipruritic and antihistamine in the ethylenediamine class. It can be used in the treatment of asthma, hay fever, rhinitus and urticaria but is now less common as it has been replaced by newer antihistamines. This drug is sold in 50 mg tablets, which are usually green in colour. Tripellenamine is marketed by Novartis under the trade name Pyribenzamine.

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

[edit] Side effects

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

[edit] Recreational use

Tripelennamine is sometimes abused recreationally in combination with the opiate pentazocine ("T's & Blues"), morphine ("Blue Velvet") and narcotic cough syrups. 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, meclizine, 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.

v • d • e Antipruritics (D04) Antihistamines for topical use Thonzylamine - Mepyramine - Thenalidine - Tripelennamine - Chloropyramine - Promethazine - Tolpropamine - Dimetindene - Clemastine - Bamipine - Isothipendyl - Diphenhydramine - Chlorphenoxamine Anesthetics for topical use Lidocaine - Cinchocaine - Oxybuprocaine - Benzocaine - Quinisocaine - Tetracaine - Pramocaine

v • d • e Antihistamines (primarily R06) Aminoalkyl ethers Bromazine/Bromodiphenhydramine • Carbinoxamine • Clemastine • Chlorphenoxamine • Diphenylpyraline • Diphenhydramine • Doxylamine • Orphenadrine • Phenyltoloxamine Substituted alkylamines Brompheniramine • Chlorphenamine • Dexbrompheniramine • Dexchlorpheniramine • Dimetindene • Pheniramine • Talastine Substituted ethylenediamines Chloropyramine • Histapyrrodine • Mepyramine • Methapyrilene • Tripelennamine (Pyribenzamine) Phenothiazine derivatives Alimemazine • Hydroxyethylpromethazine • Isothipendyl • Mequitazine • Methdilazine • Oxomemazine • Promethazine Piperazine derivatives Buclizine • Cetirizine • Chlorcyclizine • Cinnarizine • Cyclizine • Hydroxyzine • Levocetirizine • Meclizine • Niaprazine • Oxatomide Others for systemic use Antazoline • Azatadine • Bamipine • Cyproheptadine • Deptropine • Dimebon • Ebastine • Epinastine • Ketotifen • Mebhydrolin • Mizolastine • Phenindamine • Pimethixene • Pyrrobutamine • Rupatadine • Triprolidine • selective (Acrivastine • Astemizole • Azelastine • Desloratadine • Fexofenadine • Loratadine • Terfenadine) For topical use Bamipine • Chloropyramine • Chlorphenoxamine • Clemastine • Dimetindene • Diphenhydramine • Isothipendyl • Mepyramine • Promethazine • Thenalidine Antiallergic agents excluding corticosteroids Antazoline • Azelastine Other antiallergics Emedastine • Epinastine • Ketotifen • Montelukast • Olopatadine