Lamotrigine (CAS 84057-84-1) — formula C9H7Cl2N5, molecular weight 256.09; category organic chemicals.
| CAS Number | 84057-84-1 |
|---|---|
| Molecular Formula | C9H7Cl2N5 |
| Molecular Weight | 256.09 |
| Melting Point | 177-181 |
| Boiling Point | 503.1±60.0 |
| LogP | 1.93 |
| Applications | Uses: MEDICATION, Anticonvulsants, Calcium Channel Blockers, Excitatory Amino Acid Antagonists, Voltage-Gated Sodium Channel Blockers, Use (kg) in Switzerland (2009): >1000, Use (kg, approx.) in Germany (2009): >7500, Use (kg) in USA (2002): 10500, Consumption (g per capita) in Switzerland (2009): 0.13, Consumption (g per capita, approx.) in Germany (2009): 0.092, Consumption (g per capita) in the USA (2002): 0.037, Excretion rate: 0.1, Calculated removal (%): 11, For the adjunctive treatment of partial seizures in epilepsy and generalized seizures of Lennox-Gastaut syndrome. Also for the maintenance treatment of bipolar I disorder and depression. Off-label uses include the treatment of peripheral neuropathy, trigeminal neuralgia, cluster headaches, migraines, and reducing neuropathic pain. (A308, L1155), Use Classification: Pharmaceuticals, Methods of Manufacturing: Reaction of 2, 3-dichlorobenzoyl chloride with cyanide ion forms the benzoylcyanide derivative that is then treated with aminoguanidine to form a Schiff base through loss of water between the carbonyl group and the one primary amine function of the guanidine. Ring closure by addition of the lone free primary amino group remaining on the guanidine moiety of the nitrile function is accomplished by base catalysis and yields the product., The reaction of the Grignard compound of 2, 3-dichloroiodobenzene with CO2 in diethyl ether gives 2, 3-dichlorobenzoic acid, which is converted to the corresponding acyl chloride by refluxing with SOCl2. The reaction of 2, 3-dichlorobenzoyl chloride with cuprous cyanide and KI in refluxing xylene yields 2, 3-dichlorobenzoyl cyanide. Finally, this compound is cyclized with aminoguanidine in DMSO to yield lamotrigine., Hydrogenation of 2, 3-dichloronitrobenzene with H2 over Raney nickel in methanol gives 2, 3-dichloroaniline, which is diazotized with NaNO2 and HCl and treated with CuCN to yield 2, 3-dichlorobenzonitrile. Hydrolysis of the nitrile with NaOH in refluxing methanol, water affords 2, which is treated with hot SOCl2 to provide the corresponding acyl chloride. Reaction of 2, 3-dichlorobenzoyl chloride with CuCN and KI in refluxing chlorobenzene gives 2, 3-dichlorobenzoyl cyanide, which is condensed with aminoguanidine by means of H2SO4, TsOH in hot toluene to yield 2, 3-dichlorobenzoyl cyanide amidinohydrazone. Finally, this compound is cyclized by treatment with NaOMe in refluxing methanol to yield lamotrigine., Preparation: M. G. Baxter et al., European Patent Office patent 21121 (1981 to Wellcome Foundation), D. A. Sawyer et al., USA patent 4602017 (1986)., Formulations, Preparations: Table: Lamotrigine Preparations [Table#7220] |
| Category | Organic Chemicals |
Documented applications: Uses: MEDICATION, Anticonvulsants, Calcium Channel Blockers, Excitatory Amino Acid Antagonists, Voltage-Gated Sodium Channel Blockers, Use (kg) in Switzerland (2009): >1000, Use (kg, approx.) in Germany (2009): >7500, Use (kg) in USA (2002): 10500, Consumption (g per capita) in Switzerland (2009): 0.13, Consumption (g per capita, approx.) in Germany (2009): 0.092, Consumption (g per capita) in the USA (2002): 0.037, Excretion rate: 0.1, Calculated removal (%): 11, For the adjunctive treatment of partial seizures in epilepsy and generalized seizures of Lennox-Gastaut syndrome. Also for the maintenance treatment of bipolar I disorder and depression. Off-label uses include the treatment of peripheral neuropathy, trigeminal neuralgia, cluster headaches, migraines, and reducing neuropathic pain. (A308, L1155), Use Classification: Pharmaceuticals, Methods of Manufacturing: Reaction of 2, 3-dichlorobenzoyl chloride with cyanide ion forms the benzoylcyanide derivative that is then treated with aminoguanidine to form a Schiff base through loss of water between the carbonyl group and the one primary amine function of the guanidine. Ring closure by addition of the lone free primary amino group remaining on the guanidine moiety of the nitrile function is accomplished by base catalysis and yields the product., The reaction of the Grignard compound of 2, 3-dichloroiodobenzene with CO2 in diethyl ether gives 2, 3-dichlorobenzoic acid, which is converted to the corresponding acyl chloride by refluxing with SOCl2. The reaction of 2, 3-dichlorobenzoyl chloride with cuprous cyanide and KI in refluxing xylene yields 2, 3-dichlorobenzoyl cyanide. Finally, this compound is cyclized with aminoguanidine in DMSO to yield lamotrigine., Hydrogenation of 2, 3-dichloronitrobenzene with H2 over Raney nickel in methanol gives 2, 3-dichloroaniline, which is diazotized with NaNO2 and HCl and treated with CuCN to yield 2, 3-dichlorobenzonitrile. Hydrolysis of the nitrile with NaOH in refluxing methanol, water affords 2, which is treated with hot SOCl2 to provide the corresponding acyl chloride. Reaction of 2, 3-dichlorobenzoyl chloride with CuCN and KI in refluxing chlorobenzene gives 2, 3-dichlorobenzoyl cyanide, which is condensed with aminoguanidine by means of H2SO4, TsOH in hot toluene to yield 2, 3-dichlorobenzoyl cyanide amidinohydrazone. Finally, this compound is cyclized by treatment with NaOMe in refluxing methanol to yield lamotrigine., Preparation: M. G. Baxter et al., European Patent Office patent 21121 (1981 to Wellcome Foundation), D. A. Sawyer et al., USA patent 4602017 (1986)., Formulations, Preparations: Table: Lamotrigine Preparations [Table#7220].
Lamotrigine is a carbon-based organic compound with CAS registry number 84057-84-1 and molecular formula C9H7Cl2N5 (molecular weight 256.09), belonging to the organic chemicals segment of chemical raw materials.
CAS number: 84057-84-1
Its molecular formula C9H7Cl2N5 comprises 9 C, 7 H, 2 Cl, 5 N atoms.
Also known as: Lamotrigine · 拉莫三嗪
Category: organic chemicals
The CAS registry number of Lamotrigine is 84057-84-1.
Molecular formula C9H7Cl2N5, molecular weight 256.09.
It is also registered under: Lamotrigine, 拉莫三嗪.
Recorded applications: Uses: MEDICATION, Anticonvulsants, Calcium Channel Blockers, Excitatory Amino Acid Antagonists, Voltage-Gated Sodium Channel Blockers, Use (kg) in Switzerland (2009): >1000, Use (kg, approx.) in Germany (2009): >7500, Use (kg) in USA (2002): 10500, Consumption (g per capita) in Switzerland (2009): 0.13, Consumption (g per capita, approx.) in Germany (2009): 0.092, Consumption (g per capita) in the USA (2002): 0.037, Excretion rate: 0.1, Calculated removal (%): 11, For the adjunctive treatment of partial seizures in epilepsy and generalized seizures of Lennox-Gastaut syndrome. Also for the maintenance treatment of bipolar I disorder and depression. Off-label uses include the treatment of peripheral neuropathy, trigeminal neuralgia, cluster headaches, migraines, and reducing neuropathic pain. (A308, L1155), Use Classification: Pharmaceuticals, Methods of Manufacturing: Reaction of 2, 3-dichlorobenzoyl chloride with cyanide ion forms the benzoylcyanide derivative that is then treated with aminoguanidine to form a Schiff base through loss of water between the carbonyl group and the one primary amine function of the guanidine. Ring closure by addition of the lone free primary amino group remaining on the guanidine moiety of the nitrile function is accomplished by base catalysis and yields the product., The reaction of the Grignard compound of 2, 3-dichloroiodobenzene with CO2 in diethyl ether gives 2, 3-dichlorobenzoic acid, which is converted to the corresponding acyl chloride by refluxing with SOCl2. The reaction of 2, 3-dichlorobenzoyl chloride with cuprous cyanide and KI in refluxing xylene yields 2, 3-dichlorobenzoyl cyanide. Finally, this compound is cyclized with aminoguanidine in DMSO to yield lamotrigine., Hydrogenation of 2, 3-dichloronitrobenzene with H2 over Raney nickel in methanol gives 2, 3-dichloroaniline, which is diazotized with NaNO2 and HCl and treated with CuCN to yield 2, 3-dichlorobenzonitrile. Hydrolysis of the nitrile with NaOH in refluxing methanol, water affords 2, which is treated with hot SOCl2 to provide the corresponding acyl chloride. Reaction of 2, 3-dichlorobenzoyl chloride with CuCN and KI in refluxing chlorobenzene gives 2, 3-dichlorobenzoyl cyanide, which is condensed with aminoguanidine by means of H2SO4, TsOH in hot toluene to yield 2, 3-dichlorobenzoyl cyanide amidinohydrazone. Finally, this compound is cyclized by treatment with NaOMe in refluxing methanol to yield lamotrigine., Preparation: M. G. Baxter et al., European Patent Office patent 21121 (1981 to Wellcome Foundation), D. A. Sawyer et al., USA patent 4602017 (1986)., Formulations, Preparations: Table: Lamotrigine Preparations [Table#7220].
Category: Organic Chemicals.
Independent reference data for Lamotrigine (CAS 84057-84-1), compiled from public chemistry databases.
| CAS 号 | 84057-84-1 |
|---|---|
| PubChem CID | 3878 |
| 分子式 | C9H7Cl2N5 |
| IUPAC 名称 | 6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine |
| UNII（FDA） | U3H27498KS |
| Molecular Weight | 256.09 |
|---|---|
| XLogP3 | 1.4 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 1 |
| Exact Mass | 255.0078506 |
| Monoisotopic Mass | 255.0078506 |
| Topological Polar Surface Area | 90.7 |
| Heavy Atom Count | 16 |
| Boiling Point | 503.1±60.0 |
|---|---|
| Melting Point | 177-181 |
| Melting Point | 216-218 °C (uncorr) |
| Melting Point | 216 - 218 °C (uncorr.) |
| Solubility | 0.17 |
| Solubility | In water, 170 mg/L at 25 °C |
| Solubility | 4.88e-01 g/L |
| LogP | 1.93 |
| LogP | log Kow = 2.57 |
| LogP | 2.5 |
lamotrigine; 84057-84-1; 6-(2,3-Dichlorophenyl)-1,2,4-triazine-3,5-diamine; Lamictal; Lamictal Cd; Lamotrigina; Lamictal XR; Lamotriginum; BW 430C; 3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine; BW-430C; Lamictal ODT; 1,2,4-Triazine-3,5-diamine, 6-(2,3-dichlorophenyl)-; 3,5-Diamino-6-(2,3-dichlorophenyl)-as-triazine; DTXSID2023195; BW430C
| 已通报的危害声明 | H301 (100%), H412 (19.1%), H319 (100%), H336 (100%), H361 (100%), H362 (100%), H410 (100%) |
|---|
拉莫三嗪 · CAS 84057-84-1 · C9H7Cl2N5. UNII U3H27498KS. Boiling Point: 503.1±60.0; Melting Point: 177-181; Melting Point: 216-218 °C (uncorr).
Source: PubChem / Wikidata; the batch COA governs where values differ.
Supplier: Jinan Shenghe Chemical Co., Ltd.
中文页面: 拉莫三嗪