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| CAS No.: | 91-81-6 |
|---|---|
| Name: | Tripelennamine |
| Article Data: | 5 |
| Molecular Structure: | |
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| Formula: | C16H21 N3 |
| Molecular Weight: | 255.363 |
| 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 |
| EINECS: | 202-100-1 |
| Density: | 1.0683 (rough estimate) |
| Melting Point: | 25°C |
| Boiling Point: | 185 - 190 C at 1.7 mm Hg |
| Solubility: | Toxicity data "> high
Stability
Toxicology
Toxicity data |
| Appearance: | oily liquid |
| Hazard Symbols: | Toxic by ingestion. |
| 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. |
| PSA: | 19.37000 |
| LogP: | 2.64980 |
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- 945683-37-41-butyl-2,3-dimethylimidazolium octanesulfate
- 946052-36-41-Butyl-3-methylpyridinium methanesulfonate
- 942196-38-51-Hexyl-3-methylpyridinium hexafluorophosphat
- 929897-32-51-hexyl-4-methylpridine hexafluorophosphate
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With TurboGrignard In tetrahydrofuran at 0 - 25℃; for 8h; Inert atmosphere; | 74% |
- 91-81-6
tripelennamine
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| 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
- 91-81-6
tripelennamine
| Conditions | Yield |
|---|---|
| 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; |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With XAD-2 ion-exchange resin; sodium hydrogencarbonate In chloroform; water for 120h; Ambient temperature; | 16% |
| Conditions | Yield |
|---|---|
| With acetone |
- 91-81-6
tripelennamine
- 60317-19-3
N'-benzyl-N,N-dimethyl-N'-[2]pyridyl-ethylenediamine-N-oxide
| Conditions | Yield |
|---|---|
| With ethanol; dihydrogen peroxide |
- 91-81-6
tripelennamine
| Conditions | Yield |
|---|---|
| With oxygen; palladium on activated charcoal In methanol for 24h; Ambient temperature; |
- Total:26 Page 1 of 1 1
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Chemistry
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
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.
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.
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. |
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.
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 .