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| CAS No.: | 27262-47-1 |
|---|---|
| Name: | 1-Butyl-N-(2,6-dimethylphenyl)-piperidine-2-carboxamide |
| Molecular Structure: | |
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|
| Formula: | C18H28N2O |
| Molecular Weight: | 288.433 |
| Synonyms: | 2-Piperidinecarboxamide,1-butyl-N-(2,6-dimethylphenyl)-, (S)-;2',6'-Pipecoloxylidide, 1-butyl-, (-)-(8CI);(-)-(S)-Bupivacaine;(-)-Bupivacaine;(S)-(-)-Bupivacaine;(S)-Bupivacaine;Chirocain;L-(-)-Bupivacaine;Levobupivacaine; |
| EINECS: | 1533716-785-6 |
| Density: | 1.032 g/cm3 |
| Melting Point: | 254ºC (dec.)(lit.) |
| Boiling Point: | 423.4 °C at 760 mmHg |
| Flash Point: | 209.9 °C |
| Hazard Symbols: |
 Xn, T+
|
| PSA: | 32.34000 |
| LogP: | 4.70940 |
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Specification
The IUPAC name of L(-)-Bupivacaine is (2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide. With the CAS registry number 27262-47-1, it is also named as Levobupivacaine. The classification codes are Anesthetics; Anesthetics, Local; Central Nervous System Agents; Central Nervous System Depressants; Drug / Therapeutic Agent; Peripheral Nervous System Agents; Sensory System Agents. It is highly toxic. And it will produce toxic nitrogen oxide fumes by heating, so the storage environment should be ventilate, low-temperature and dry. Keep L(-)-Bupivacaine separate from raw materials of food.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.64; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.47; (4)ACD/LogD (pH 7.4): 3.15; (5)ACD/BCF (pH 5.5): 2.34; (6)ACD/BCF (pH 7.4): 111.54; (7)ACD/KOC (pH 5.5): 15.49; (8)ACD/KOC (pH 7.4): 739.57; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.547; (13)Molar Refractivity: 88.62 cm3; (14)Molar Volume: 279.2 cm3; (15)Polarizability: 35.13×10-24 cm3; (16)Surface Tension: 41.5 dyne/cm; (17)Enthalpy of Vaporization: 67.78 kJ/mol; (18)Vapour Pressure: 2.24E-07 mmHg at 25°C; (19)Rotatable Bond Count: 5; (20)Tautomer Count: 2; (21)Exact Mass: 288.220164; (22)MonoIsotopic Mass: 288.220164; (23)Topological Polar Surface Area: 32.3; (24)Heavy Atom Count: 21.
Uses of L(-)-Bupivacaine: It is a local anaesthetic drug belonging to the amino amide group. And it is used for local anaesthesia including infiltration, nerve block, ophthalmic, epidural and intrathecal anaesthesia in adults; and infiltration analgesia in children.
People can use the following data to convert to the molecule structure.
1. SMILES:O=C(Nc1c(cccc1C)C)[C@H]2N(CCCC)CCCC2
2. InChI:InChI=1/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)/t16-/m0/s1.
The following are the toxicity data which has been tested.
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intravenous | 9600ug/kg (9.6mg/kg) | Acta Pharmacologica et Toxicologica. Vol. 31, Pg. 273, 1972. | |
| mouse | LD50 | subcutaneous | 100mg/kg (100mg/kg) | Acta Pharmacologica et Toxicologica. Vol. 31, Pg. 273, 1972. | |
| rabbit | LD50 | intratracheal | 14mg/kg (14mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 78, 1976. | |
| rabbit | LD50 | parenteral | > 120mg/kg (120mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 26, Pg. 78, 1976. | |
| rabbit | LDLo | intravenous | 9700ug/kg (9.7mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Acta Pharmacologica et Toxicologica. Vol. 31, Pg. 273, 1972. |
| rat | LD50 | intravenous | 7200ug/kg (7.2mg/kg) | Acta Pharmacologica et Toxicologica. Vol. 31, Pg. 273, 1972. | |
| rat | LD50 | subcutaneous | 52mg/kg (52mg/kg) | Acta Pharmacologica et Toxicologica. Vol. 31, Pg. 273, 1972. |