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302-41-0

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Basic Information
CAS No.: 302-41-0
Name: piritramide
Molecular Structure:
Molecular Structure of 302-41-0 (piritramide)
Formula: C27H34N4O
Molecular Weight: 430.593
Synonyms: 1-(3,3-Diphenyl-3-cyanopropyl)-4-piperidino-4-piperidinecarboxamide;1'-(3-Cyano-3,3-diphenylpropyl)-[1,4'-bipiperidine]-4'-carboxamide;2,2-Diphenyl-4-(4-piperidino-4-carbamoylpiperidino)butyronitrile;2,2-Diphenyl-4-[4-(1-piperidino)-4-carbamoyl-1-piperidino]butyronitrile;Dipidolor;Dipiritramide;Pirdolan;Piridolan;Pirinitramide;Piritramide;R3365;
EINECS: 206-124-3
Density: 1.15 g/cm3
Melting Point: 149-150°
Boiling Point: 642.5 °C at 760 mmHg
Flash Point: 342.3 °C
Solubility: 0.491 mg/L 25 °C in water
PSA: 73.36000
LogP: 4.26828
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History

Piritramide (CAS NO.302-41-0) is also known as pirinitramide. Its closest chemical relatives amongst well-known drugs are diphenoxylate (Lomotil) and bezitramide (Burgodin).
Piritramide's most common trade name is Dipidolor and it is used most heavily in the Netherlands, Denmark, and Germany.
Piritramide is a strong opioid and therefore is regulated much the same as morphine in all known jurisdictions. It was never introduced in the United States and is therefore a Schedule I/Narcotic controlled substance. It is listed under international treaties and other laws such as the German Betäubungsmittelgesetz, the Austrian Suchtgiftmittelgesetz, the Opium Laws of various other European countries, Canadian controlled substances act, UK Misuse of Drugs Act of 1971, and equivalents elsewhere. Strangely enough, bezitramide, which is not currently marketed in the United States is a Schedule II/Narcotic controlled substance.
Piritramide has a small but dedicated community of recreational users and it has the street names P, Dip (rhymes with "pipe")and Pierrette.

Consensus Reports

Cyanide and its compounds are on the Community Right-To-Know List.

Specification

The Piritramide, with the CAS registry number 302-41-0, is also known as (1,4'-Bipiperidine)-4'-carboxamide, 1'-(3-cyano-3,3-diphenylpropyl)-. Its molecular formula is C27H34N4O and its IUPAC name is 1-(3-cyano-3,3-diphenylpropyl)-4-piperidin-1-ylpiperidine-4-carboxamide. Additionally, its classification codes are Analgesics; Analgesics, opioid; Central Nervous System Agents; Central Nervous System Depressants; Drug / Therapeutic Agent; Narcotics; Peripheral Nervous System Agents; Sensory System Agents. It's a diphenylpropylamine with intense narcotic analgesic activity of long duration. It is a derivative of meperidine with similar activity and usage.

Other characteristics of the Piritramide can be summarised as followings: (1)ACD/LogP: 4.21; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2; (4)ACD/LogD (pH 7.4): 3.69; (5)ACD/BCF (pH 5.5): 5.77; (6)ACD/BCF (pH 7.4): 284.04; (7)ACD/KOC (pH 5.5): 28.72; (8)ACD/KOC (pH 7.4): 1414.87; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 50.58 Å2; (13)Index of Refraction: 1.59; (14)Molar Refractivity: 126.27 cm3; (15)Molar Volume: 374.1 cm3; (16)Polarizability: 50.05×10-24cm3; (17)Surface Tension: 52.9 dyne/cm; (18)Density: 1.15 g/cm3; (19)Flash Point: 342.3 °C; (20)Enthalpy of Vaporization: 94.82 kJ/mol; (21)Boiling Point: 642.5 °C at 760 mmHg; (22)Vapour Pressure: 2.13E-16 mmHg at 25°C.

You can still convert the following datas into molecular structure: 
1.SMILES: N#CC(c1ccccc1)(c2ccccc2)CCN4CCC(C(=O)N)(N3CCCCC3)CC4
2.InChI: InChI=1/C27H34N4O/c28-22-26(23-10-4-1-5-11-23,24-12-6-2-7-13-24)14-19-30-20-15-27(16-21-30,25(29)32)31-17-8-3-9-18-31/h1-2,4-7,10-13H,3,8-9,14-21H2,(H2,29,32)
3.InChIKey: IHEHEFLXQFOQJO-UHFFFAOYAS

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 subcutaneous > 10mg/kg (10mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 13, Pg. 513, 1961.
dog LD50 subcutaneous > 40mg/kg (40mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 13, Pg. 513, 1961.
monkey LD50 subcutaneous > 10mg/kg (10mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 13, Pg. 513, 1961.
mouse LD50 intravenous 30700ug/kg (30.7mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION Farmakologiya i Toksikologiya Vol. 54(5), Pg. 59, 1991.
mouse LD50 oral > 320mg/kg (320mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 13, Pg. 513, 1961.
mouse LD50 subcutaneous 280mg/kg (280mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION Journal of Pharmacy and Pharmacology. Vol. 13, Pg. 513, 1961.
rat LD50 intravenous 13mg/kg (13mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION Journal of Pharmacy and Pharmacology. Vol. 13, Pg. 513, 1961.
rat LD50 oral 320mg/kg (320mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION Journal of Pharmacy and Pharmacology. Vol. 13, Pg. 513, 1961.