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TRIPELENNAMINE

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Name

TRIPELENNAMINE

EINECS 202-100-1
CAS No. 91-81-6 Density 1.0683 (rough estimate)
PSA 19.37000 LogP 2.64980
Solubility high

Stability

    Stable. Incompatible with strong oxidizing agents.

Toxicology

    Poisonous by ingestion. May be harmful by skin contact or if inhaled.

    Toxicity data

Melting Point 25°C
Formula C16H21 N3 Boiling Point 185 - 190 C at 1.7 mm Hg
Molecular Weight 255.363 Flash Point N/A
Transport Information N/A Appearance oily liquid
Safety Poison by ingestion and intraperitoneal routes. Human mutation data reported. Has been implicated in aplastic anemia. Used as an antihistamine. Addicts have added it to paregoric to make “blue velvet,” which can cause euphoria by injection. When heated to decomposition it emits toxic fumes of NOx. Risk Codes N/A
Molecular Structure Molecular Structure of 91-81-6 (Tripelennamine) Hazard Symbols Toxic by ingestion.
Synonyms

1,2-Ethanediamine,N,N-dimethyl-N'-(phenylmethyl)-N'-2-pyridinyl- (9CI); Ethylenediamine, N-benzyl-N',N'-dimethyl-N-2-pyridyl-(4CI); Pyridine, 2-[benzyl[2-(dimethylamino)ethyl]amino]- (8CI);2-[Benzyl(2-dimethylaminoethyl)amino]pyridine; Benzoxale; Cizaron;N,N-Dimethyl-N'-benzyl-N'-(a-pyridyl)ethylenediamine; N-Benzyl-N',N'-dimethyl-N-2-pyridylethylenediamine;NSC 118946; PBZ; Pyribenzamin; Pyribenzamine; Pyrinamine base; Resistamine;Tonaril; Tripelenamine; Tripelennamin; Tripelennamine

Article Data 5

TRIPELENNAMINE Synthetic route

872298-31-2

2-(N-benzyl-pyridin-2-yl-amino)ethanol

124-40-3

dimethyl amine

91-81-6

tripelennamine

Conditions
ConditionsYield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; bis[2-(diphenylphosphino)phenyl] ether In toluene at 20℃; Inert atmosphere; Reflux;75%
874493-33-1

pyridin-2-yl N,N,N',N'-tetramethyldiamidophosphate

103-55-9

N,N-dimethyl-N'-benzyl-1,2-ethanediamine

91-81-6

tripelennamine

Conditions
ConditionsYield
With TurboGrignard In tetrahydrofuran at 0 - 25℃; for 8h; Inert atmosphere;74%

N-benzyl-N-(2-(dimethylamino)ethyl)pyridine-2-sulfonamide

91-81-6

tripelennamine

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylborane; sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 5,5-dimethyl-1,3-cyclohexadiene at 60℃; for 16h; Glovebox; Inert atmosphere; Sealed tube;49%
109-09-1

2-chloropyridine

91-81-6

tripelennamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 12 h / 140 °C / Inert atmosphere; Sealed tube
2.1: lithium amide / acetonitrile / 0.08 h / Inert atmosphere
2.2: 8 h / Inert atmosphere; Reflux
View Scheme
23826-72-4

N,N-dimethyl-N'-(pyridine-2-yl)ethane-1,2-diamine

benzyl halide

benzyl halide

91-81-6

tripelennamine

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-N'-(pyridine-2-yl)ethane-1,2-diamine With lithium amide In acetonitrile for 0.0833333h; Inert atmosphere;
Stage #2: benzyl halide In acetonitrile for 8h; Inert atmosphere; Reflux;
142-08-5

2-hydroxypyridin

91-81-6

tripelennamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dmap; triethylamine / tetrahydrofuran / 12 h / 25 °C / Inert atmosphere
2: TurboGrignard / tetrahydrofuran / 8 h / 0 - 25 °C / Inert atmosphere
View Scheme
91-81-6

tripelennamine

21085-72-3

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

83708-12-7

[2-(Benzyl-pyridin-2-yl-amino)-ethyl]-((2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxy-tetrahydro-pyran-2-yl)-dimethyl-ammonium; chloride

Conditions
ConditionsYield
With XAD-2 ion-exchange resin; sodium hydrogencarbonate In chloroform; water for 120h; Ambient temperature;16%
91-81-6

tripelennamine

105-36-2

ethyl bromoacetate

ethoxycarbonylmethyl-[2-(benzyl-[2]pyridyl-amino)-ethyl]-dimethyl-ammonium; bromide

Conditions
ConditionsYield
With acetone
91-81-6

tripelennamine

60317-19-3

N'-benzyl-N,N-dimethyl-N'-[2]pyridyl-ethylenediamine-N-oxide

Conditions
ConditionsYield
With ethanol; dihydrogen peroxide
91-81-6

tripelennamine

N-Benzyl-N'-methyl-N-pyridin-2-yl-ethane-1,2-diamine

Conditions
ConditionsYield
With oxygen; palladium on activated charcoal In methanol for 24h; Ambient temperature;

TRIPELENNAMINE Chemical Properties

Product Name: Tripelennamine (CAS NO.91-81-6)


Molecular Formula: C16H21N3
Molecular Weight: 255.40g/mol
Mol File: 91-81-6.mol
Einecs: 202-100-1
Appearance: Oily liquid with an amine odor
Storage Temperature: 387.8 °C at 760 mmHg
Flash Point: 188.3 °C
Stability: Stable. Incompatible with strong oxidizing agents
Surface Tension: 46.1 dyne/cm
Enthalpy of Vaporization: 63.69 kJ/mol
Vapour Pressure: 3.21E-06 mmHg at 25°C
XLogP3-AA: 3.3
H-Bond Donor: 0
H-Bond Acceptor: 3

TRIPELENNAMINE History

 Tripelennamine (CAS NO.91-81-6) 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.

TRIPELENNAMINE Uses

 Tripelennamine (CAS NO.91-81-6) is sometimes abused recreationally in combination with the synthetic opioid pentazocine ,or morphine , by preparing an injection containing both agents; tripelennamine is also used with cough syrups and analgesic solid preparations containing opioids including codeine, propoxyphene, dextropropoxyphene, hydrocodone, ethylmorphine , paregoric, benzylmorphine, tramadol ,oxycodone ,and dihydrocodeine and its derivatives. hydromorphone ,oxymorphone ,and solid forms of methadone by either method.
It is dangerous to combine an opiate with a sedating antihistamine via injection, although the use of antihistamines 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.
Like many of the first-generation antihistamines of the ethanolamine and alkylamine classes, tripelennamine and other members of its chemical class  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.

TRIPELENNAMINE Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intraperitoneal 64mg/kg (64mg/kg)   Therapie. Vol. 28, Pg. 767, 1973.
mammal (species unspecified) LD50 subcutaneous 61mg/kg (61mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 7, Pg. 131, 1957.
mouse LD50 intraperitoneal 43mg/kg (43mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 7, Pg. 237, 1957.
mouse LD50 intravenous 23mg/kg (23mg/kg)   Japanese Journal of Toxicology. Vol. 4, Pg. 105, 1991.
mouse LD50 oral 152mg/kg (152mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 7, Pg. 237, 1957.
rat LDLo intraperitoneal 37mg/kg (37mg/kg)   Toxicology and Applied Pharmacology. Vol. 1, Pg. 156, 1959.

TRIPELENNAMINE Safety Profile

Poison by ingestion and intraperitoneal routes. Human mutation data reported. Has been implicated in aplastic anemia. Used as an antihistamine. Addicts have added it to paregoric to make “blue velvet,” which can cause euphoria by injection. When heated to decomposition it emits toxic fumes of NOx.

TRIPELENNAMINE Specification

 Tripelennamine ,its CAS NO. is 91-81-6,the synonyms is Tripelennamine ;1,2-Ethanediamine, N,N-dimethyl-N-(phenylmethyl)-N-2-pyridinyl- ; Pyribenzamine ; Benzoxale ; N,N-Dimethyl-N'-(phenylmethyl)-N'-(2-pyridinyl)-1,2-ethanediamine ; Resistamine ; Tonaril ; Tripelenamine .

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