カリソプロドール

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識別子と物理属性

CAS No.	78-44-4
分子式	C12H24N2O4
平均分子量	260.33 g/mol
単同位体質量	260.17360725 g/mol
SMILES	CCCC(C)(COC(N)=O)COC(=O)NC(C)C
InChIKey	OFZCIYFFPZCNJE-UHFFFAOYSA-N
PubChem CID	2576
ChEMBL	CHEMBL1233
ChEBI	CHEBI:3419
EC No.	201-118-7
DTXSID	DTXSID8024733
現地名	カリソプロドール

化学・物理的性質

XLogP	1.9
極性表面積	90.7
水素結合供与体数	2
水素結合受容体数	4
回転可能結合数	9
重原子数	18
形式電荷	0
複雑度	281
物質分類	Pharmaceutical
医薬品	DEA NFLIS-Drug Category -> Depressants and TranquilizersDEA Schedule IV Controlled Substance -> DepressantsPharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
LogP（分配係数）	2.12.01
味	Slightly bitter taste
Color/Form	Crystals
溶解度	less than 1 mg/mL at 67.1 °F (NTP, 1992)slightly solubleSoluble in most common organic solventspractically insoluble in vegetable oilsIn water, 30 mg/100 mL at 25 °C140 mg/100 mL water at 50 °C7.92e-01 g/L水に非常に溶けにくく、アセトン、アルコール、塩化メチレンに溶けやすい。<0.1 g/100 mL で 19.5 ºC
Human Drugs	Breast FeedingLactationMilk, HumanMuscle Relaxants, CentralFDA approved drugs -> Active ingredientPharmaceuticals
融点	198 to 199 °F (NTP, 1992)92 °C92 - 93 °C92-92°C
Physical Description	Carisoprodol is a white powder. (NTP, 1992)Solid
Stability/Shelf Life	STABLE IN DIL ACIDS & ALKALIES.
Dissociation Constants	15.06 (Strongest acidic)
Collision Cross Section	172.2 Å² [M+Na]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID8024733]149.1 Å² [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]167.96 Å² [M+Na]+ [CCS Type: TW
沸点	403.59°C (rough estimate)
密度	1.1035 (rough estimate)
屈折率	1.4560 (estimate)
貯蔵条件	2-8°C
外観・状態	個体
pKa（酸解離定数）	pKa 4.2 (Uncertain)
色	ホワイトからオフホワイト
由来生物	rabbit
ヘンリー定数	1.4×104 mol/(m3Pa) at 25℃, HSDB (2015)
BCS Class	2/4
主な用途	医薬品（低分子化合物）
InChI	InChI=1S/C12H24N2O4/c1-5-6-12(4,7-17-10(13)15)8-18-11(16)14-9(2)3/h9H,5-8H2,1-4H3,(H2,13,15)(H,14,16)
InChIKey	OFZCIYFFPZCNJE-UHFFFAOYSA-N
SMILES	C(OCC(COC(N)=O)(C)CCC)(=O)NC(C)C
CAS データベース	78-44-4(CAS DataBase Reference)
NISTの化学物質情報	Carisoprodol(78-44-4)
EPAの化学物質情報	Carisoprodol (78-44-4)

化学的特性

White Solid

安全性と法規制

GHS 分類	WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 43 reports by companies from 1 notifications to the ECHA C&L Inventory.
規制情報	DEA schedule IV controlled substance
その他の安全情報	IMAP assessments - Carbamic acid, (1-methylethyl)-, 2-[[(aminocarbonyl)oxy]methyl]-2-methylpentyl ester: Environment tier I assessment
火災危険	Flash point data for this chemical are not available, but it it probably combustible. (NTP, 1992)
健康有害性	SYMPTOMS: The most common symptoms of exposure to this chemical are drowsiness and hives. Other symptoms may include nausea, vomiting, epigastric distress, vertigo, ataxia, tremors, agitation, irritability, headache, insomnia, fainting, hiccups, visual disturbances, asthma, fever, hypotension, excitement and paralysis. (NTP, 1992)
FDA 要件	The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including carisoprodol, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.This is notice that the Drug Enforcement Administration (DEA) will hold a hearing with respect to the proposed placement of carisoprodol in schedule IV of the Controlled Substances Act (21 U.S.C. 801, et seq.). The control of carisoprodol was initially proposed in a Notice of Proposed Rulemaking published in the Federal Register on November 17, 2009 (74 FR 59108).
反応性グループ	Carbamates
Reactivity Profile	CARISOPRODOL is a carbamate ester. Carbamates are chemically similar to, but more reactive than amides. Like amides they form polymers such as polyurethane resins. Carbamates are incompatible with strong acids and bases, and especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen is produced by the combination of active metals or nitrides with carbamates. Strongly oxidizing acids, peroxides, and hydroperoxides are incompatible with carbamates.
Air and Water Reactions	Insoluble in water.

用途

説明

Carisoprodol (Item No. 30778) is an analytical reference standard categorized as a skeletal muscle relaxant. It also has sedative properties. Carisoprodol is regulated as a Schedule IV compound in the United States. This product is intended for research and forensic applications.

使用

Muscle relaxant (skeletal) Carisoprodol has an onset of action of ca. 30min and a duration of 4–6h. It is administered orally. Presumably, it acts by inhibiting interneuronal activity in the spinal cord and the brainstem reticular formation. Clinically effective doses are accompanied by drowsiness or dizziness; its mechanism may involve sedation.Its CNS depressant effects are additive with those of ethanol and other psychotropic agents. Carisoprodol has a low potential for drug dependence.

一般的な説明

Carisoprodol, N-isopropyl-2-methyl-2-propyl-1,3-propanediol dicarbamate, 2-methyl-2-propyl-1,3-propanediol carbamate isopropylcarbamate(Soma), is the mono-N-isopropyl–substituted relative ofmeprobamate. The structure is given in the discussion ofmeprobamate. It is indicated in acute skeletomuscular conditionscharacterized by pain, stiffness, and spasm. As canbe expected, a major side effect of the drug is drowsiness.

製法・合成法

製造方法

Carisoprodol is Prepared by reaction of 2-methyl-2-propyl-1,3-pro-panediol with phosgene and ammonium hydroxide, then with isopropyl isocyanate.