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78-44-4

Basic Information
CAS No.: 78-44-4
Name: Carbamic acid, N-(1-methylethyl)-, 2-[[(aminocarbonyl)oxy]methyl]-2-methylpentyl ester
Molecular Structure:
Molecular Structure of 78-44-4 (Carbamic acid, N-(1-methylethyl)-, 2-[[(aminocarbonyl)oxy]methyl]-2-methylpentyl ester)
Formula: C12H24N2O4
Molecular Weight: 260.33
Synonyms: Carbamicacid, (1-methylethyl)-, 2-[[(aminocarbonyl)oxy]methyl]-2-methylpentyl ester(9CI);Carbamic acid, isopropyl-, 2-(hydroxymethyl)-2-methylpentyl estercarbamate (ester) (8CI);Carbamic acid, isopropyl-,2-(hydroxymethyl)-2-methylpentyl ester, carbamate (6CI);2-Methyl-2-propyl-1,3-propanediol carbamate isopropylcarbamate;Apesan;Atonalyt;Caprodat;Carisoma;Carisoprodate;Carisoprodatum;Domarax;Flexal;Isobamate;Isomeprobamate;Isoprotane;Isoprothane;Izoprotan;Mioril;N-Isopropyl-2-methyl-2-propyl-1,3-propanediol dicarbamate;NSC172124;Rela;Sanoma;Soma;Somalgit;Carisoprodol;
EINECS: 201-118-7
Density: 1.056 g/cm3
Melting Point: 92-92 oC
Boiling Point: 423.412 °C at 760 mmHg
Flash Point: 209.872 °C
Solubility: slightly soluble in water and freely soluble in alcohol, chloroform and acetone
Appearance: White powder.
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: 36
Transport Information:
PSA: 90.65000
LogP: 3.11390
Synthetic route
25462-17-3

N-Mono-isopropyl-2-methyl-2-n-propylpropane-1,3-diol carbamate

3019-71-4

Trichloroacetyl isocyanate

78-44-4

carisoprodol

Conditions
ConditionsYield
Stage #1: N-Mono-isopropyl-2-methyl-2-n-propylpropane-1,3-diol carbamate; Trichloroacetyl isocyanate In methanol; dichloromethane at 0 - 25℃; for 4h;
Stage #2: With potassium carbonate In methanol; dichloromethane at 25℃; for 4h;
96%
25462-17-3

N-Mono-isopropyl-2-methyl-2-n-propylpropane-1,3-diol carbamate

917-61-3

sodium isocyanate

78-44-4

carisoprodol

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane at -2 - 2℃; for 10h;80%
Stage #1: N-Mono-isopropyl-2-methyl-2-n-propylpropane-1,3-diol carbamate; sodium isocyanate With hydrogenchloride In dichloromethane at 0℃; for 2.5h;
Stage #2: With sodium hydrogencarbonate In dichloromethane pH=8;
75-44-5

phosgene

25462-17-3

N-Mono-isopropyl-2-methyl-2-n-propylpropane-1,3-diol carbamate

78-44-4

carisoprodol

Conditions
ConditionsYield
(i) PhNMe2, (ii) NH3; Multistep reaction;
7148-50-7

5-Methyl-5-n-propyl-1,3-dioxan-2-one

78-44-4

carisoprodol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 5 h / Heating
2: 80 percent / HCl / CH2Cl2 / 10 h / -2 - 2 °C
View Scheme
Multi-step reaction with 2 steps
2: (i) PhNMe2, (ii) NH3
View Scheme
78-26-2

2-methyl-2-propyl-1,3-propanediol

78-44-4

carisoprodol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) Na / 1.) toluene, 90 deg C, 30 min, 2.) toluene, 88-110 deg C
2: 5 h / Heating
3: 80 percent / HCl / CH2Cl2 / 10 h / -2 - 2 °C
View Scheme
Multi-step reaction with 3 steps
1.1: p-toluenesulfonyl chloride; n-butyllithium
1.2: 0 - 60 °C
2.1: C49H74AlNO4; bis(triphenylphosphoranylidene)ammonium iodide / butanone / 80 h / 100 °C / 7500.75 Torr / Autoclave; Sealed tube
3.1: dichloromethane; methanol / 4 h / 0 - 25 °C
3.2: 4 h / 25 °C
View Scheme
13911-97-2

3-methyl 3-n-propyl oxetane

78-44-4

carisoprodol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: C49H74AlNO4; bis(triphenylphosphoranylidene)ammonium iodide / butanone / 80 h / 100 °C / 7500.75 Torr / Autoclave; Sealed tube
2.1: dichloromethane; methanol / 4 h / 0 - 25 °C
2.2: 4 h / 25 °C
View Scheme
78-44-4

carisoprodol

110-82-7

cyclohexane

C18H34N2O4

Conditions
ConditionsYield
With di-tert-butyl peroxide; copper diacetate; 4,4'-di-tert-butyl-2,2'-bipyridine In acetonitrile at 25℃; for 12h; Inert atmosphere; Irradiation; chemoselective reaction;60%
91-01-0

1,1-Diphenylmethanol

78-44-4

carisoprodol

N-(Diphenylmethyl)-carisoprodol

78-44-4

carisoprodol

123-62-6

propionic acid anhydride

25648-91-3

N-Isopropyl-N'-propionyl-2-methyl-2-propyl-1,3-dicarbamoyloxy-propan

Conditions
ConditionsYield
With sulfuric acid
50-00-0

formaldehyd

78-44-4

carisoprodol

109-89-7

diethylamine

25648-95-7

N-Isopropyl-N'-diaethylamino-methyl-2-methyl-2-propyl-1,3-dicarbamoyloxy-propan

Conditions
ConditionsYield
(i), (ii) /BRN= 605268/; Multistep reaction;
78-44-4

carisoprodol

bovine serum albumin

bovine serum albumin

carisoprodol complex with bovine serum albumin

carisoprodol complex with bovine serum albumin

Conditions
ConditionsYield
In aq. phosphate buffer at 24.84℃; pH=7.4; Thermodynamic data; Temperature;
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    78-44-4

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    78-44-4

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Specification

The Carisoprodol, with the CAS registry number 78-44-4, is also known as N-Isopropyl 2-methyl-2-propyl-1,3-propanediol dicarbamate. It belongs to the product categories of Active Pharmaceutical Ingredients; API intermediates; Isotope Labeled Compounds; Intermediates & Fine Chemicals; Pharmaceuticals; Muscle Relaxants; Neurobiology; Pharmacologicals; Aliphatics; Amines. Its EINECS number is 201-118-7. This chemical's molecular formula is C12H24N2O4 and molecular weight is 260.33. What's more, its systematic name is 2-[(Carbamoyloxy)methyl]-2-methylpentyl isopropylcarbamate. Its classification codes are: (1)Central Nervous System Agents; (2)Drug / Therapeutic Agent; (3)Muscle relaxants, central; (4)Neuromuscular Agents; (5)Peripheral Nervous System Agents; (6)Relaxant [skeletal muscle]; (7)Reproductive Effect; (8)Tumor data. This chemical is harmful if swallowed. When using it, you need wear suitable protective clothing. It is a centrally acting skeletal muscle relaxant whose mechanism of action is not completely understood but may be related to its sedative actions. It is used as an adjunct in the symptomatic treatment of musculoskeletal conditions associated with painful muscle spasm.

Physical properties of Carisoprodol are:
(1)ACD/LogP: 2.099; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.10; (4)ACD/LogD (pH 7.4): 2.10; (5)ACD/BCF (pH 5.5): 23.18; (6)ACD/BCF (pH 7.4): 23.18; (7)ACD/KOC (pH 5.5): 330.23; (8)ACD/KOC (pH 7.4): 330.23; (9)#H bond acceptors: 6; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 9; (12)Polar Surface Area: 90.65 Å2; (13)Index of Refraction: 1.466; (14)Molar Refractivity: 68.247 cm3; (15)Molar Volume: 246.499 cm3; (16)Polarizability: 27.055×10-24cm3; (17)Surface Tension: 37.14 dyne/cm; (18)Density: 1.056 g/cm3; (19)Flash Point: 209.872 °C; (20)Enthalpy of Vaporization: 67.774 kJ/mol; (21)Boiling Point: 423.412 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation of Carisoprodol:
Carisoprodol can be prepared by 2-(hydroxymethyl)-2-methylpentyl isopropyl-carbamate and cyanic acid; sodium cyanate at the temperature of -2 - 2 °C. This reaction will need regent HCl and solvent CH2Cl2 with the reaction time of 10 hours. The yield is about 80%.
Carisoprodol can be prepared by 2-(hydroxymethyl)-2-methylpentyl isopropyl-carbamate and cyanic acid ; sodium cyanate at the temperature of -2 - 2 °C

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OCC(COC(=O)NC(C)C)(C)CCC)N
(2)Std. 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)
(3)Std. InChIKey: OFZCIYFFPZCNJE-UHFFFAOYSA-N

The toxicity data of Carisoprodol is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 800mg/kg (800mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 238, Pg. 92, 1960.
mouse LD50 intravenous 165mg/kg (165mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Journal of Pharmacology and Experimental Therapeutics. Vol. 127, Pg. 66, 1959.
mouse LD50 oral 1800mg/kg (1800mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Arzneimittel-Forschung. Drug Research. Vol. 12, Pg. 340, 1962.
rabbit LD50 intravenous 124mg/kg (124mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: REGIDITY

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
International Journal of Neuropharmacology. Vol. 5, Pg. 305, 1966.
rat LD50 intraperitoneal 450mg/kg (450mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE
Journal of Pharmacology and Experimental Therapeutics. Vol. 127, Pg. 66, 1959.
rat LD50 intravenous 450mg/kg (450mg/kg)   Psychopharmacology Service Center, Bulletin. Vol. 2, Pg. 17, 1963.
rat LD50 oral 1320mg/kg (1320mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE
Journal of Pharmacology and Experimental Therapeutics. Vol. 127, Pg. 66, 1959.