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CAS No.: | 671-16-9 |
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Name: | N-(1-Methylethyl)-4-((2-methylhydrazino)methyl)benzamide |
Article Data: | 9 |
Molecular Structure: | |
Formula: | C12H19 N3 O |
Molecular Weight: | 221.302 |
Synonyms: | Benzamide,N-(1-methylethyl)-4-[(2-methylhydrazino)methyl]- (9CI);p-Toluamide,N-isopropyl-a-(2-methylhydrazino)-(7CI,8CI);1-Methyl-2-[p-(isopropylcarbamoyl)benzyl]hydrazine;4-[(2-Methylhydrazino)methyl]-N-isopropylbenzamide;CB 400-497;Ibenzmethyzine;MIH;N-Isopropyl-a-(2-methylhydrazino)-p-toluamide;Procarbazine;p-(2-Methylhydrazinomethyl)-N-isopropylbenzamide; |
EINECS: | 211-582-2 |
Density: | 1.035 g/cm3 |
Boiling Point: | 384.6 °C at 760 mmHg |
Flash Point: | 148.9 °C |
Safety: | Questional carcinogen with experimental carcinogenic, neoplastigenic, and tumorigenic data. Poison by intravenous route. Moderately toxic by intraperitoneal route. Has been implicated as a brain carcinogen. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. |
PSA: | 53.16000 |
LogP: | 2.22150 |
methyl hydrazine hydrochloride
4-Formyl-benzoesaeure-isopropylamid
Procarbazine
Conditions | Yield |
---|---|
Stage #1: methyl hydrazine hydrochloride; 4-Formyl-benzoesaeure-isopropylamid In ethanol for 0.333333h; Sealed tube; Stage #2: With triethylamine In ethanol at 60℃; for 6h; Sealed tube; Stage #3: With sodium cyanoborohydride In N,N-dimethyl-formamide at 0 - 20℃; | 74% |
methylhydrazine sulfuric acid
4-Formyl-benzoesaeure-isopropylamid
Procarbazine
Conditions | Yield |
---|---|
Stage #1: methylhydrazine sulfuric acid; 4-Formyl-benzoesaeure-isopropylamid In ethanol for 0.333333h; Stage #2: With triethylamine In ethanol at 60℃; for 6h; Stage #3: With sodium cyanoborohydride In N,N-dimethyl-formamide at 0 - 20℃; | 74% |
Stage #1: methylhydrazine sulfuric acid; 4-Formyl-benzoesaeure-isopropylamid With triethylamine In ethanol at 60℃; for 6h; Stage #2: With sodium cyanoborohydride In N,N-dimethyl-formamide at 0 - 20℃; | 74% |
4-[(2-methyl-1,2-dicarbobenzoxyhydrazino)-methyl]-benzoic acid isopropylamide
Procarbazine
Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid |
Conditions | Yield |
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Multi-step reaction with 3 steps 1.1: dichloromethane 2.1: ammonium cerium (IV) nitrate; nitric acid / 24 h / 100 °C / Sealed tube 3.1: ethanol / 0.33 h / Sealed tube 3.2: 6 h / 60 °C / Sealed tube 3.3: 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: dichloromethane / 3.5 h / 20 - 40 °C 2.1: ammonium cerium (IV) nitrate; nitric acid / water / 24 h / 100 °C / Sonication 3.1: triethylamine / ethanol / 6 h / 60 °C 3.2: 0 - 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: thionyl chloride / 2 h 2.1: dichloromethane 3.1: ammonium cerium (IV) nitrate; nitric acid / 24 h / 100 °C / Sealed tube 4.1: ethanol / 0.33 h / Sealed tube 4.2: 6 h / 60 °C / Sealed tube 4.3: 0 - 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: thionyl chloride / 3 h / 80 °C 2.1: dichloromethane / 3.5 h / 20 - 40 °C 3.1: ammonium cerium (IV) nitrate; nitric acid / water / 24 h / 100 °C / Sonication 4.1: triethylamine / ethanol / 6 h / 60 °C 4.2: 0 - 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: ammonium cerium (IV) nitrate; nitric acid / 24 h / 100 °C / Sealed tube 2.1: ethanol / 0.33 h / Sealed tube 2.2: 6 h / 60 °C / Sealed tube 2.3: 0 - 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: dibromoisocyanuric acid / dichloromethane / 4 h / 20 °C 1.2: 0.17 h 2.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 15 h / Reflux 2.2: 1 h / Reflux 3.1: ethanol / 0.33 h 3.2: 6 h / 60 °C 3.3: 0 - 20 °C View Scheme |
Procarbazine
A
4-Formyl-benzoesaeure-isopropylamid
B
4-(N-Methyl-N-nitroso-hydrazonomethyl)-benzoesaeureisopropylamid
Conditions | Yield |
---|---|
With sodium nitrite In water; acetic acid for 20h; Mechanism; reactions of phenelzin and endralazin under nitrosating conditions; | A 12% B 36% |
With sodium nitrite In water; acetic acid for 20h; | A 12% B 36% |
With acetic acid; sodium nitrite |
Procarbazine
A
p-formyl-N-isopropylbenzamide methylhydrazone
B
azoprocarbazine
Conditions | Yield |
---|---|
With 4-t-butyl-1,2-benzoquinone; oxygen; tyrosinase pH=6.8; aq. phosphate buffer; Enzymatic reaction; |
(2S)-1-(2-[[(benzyloxy)carbonyl]amino]acetyl)tetrahydro-1H-pyrrole-2-carboxylic acid
Procarbazine
Conditions | Yield |
---|---|
Stage #1: (2S)-1-(2-[[(benzyloxy)carbonyl]amino]acetyl)tetrahydro-1H-pyrrole-2-carboxylic acid With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane for 0.5h; Stage #2: Procarbazine With N-ethyl-N,N-diisopropylamine In dichloromethane Overall yield = 69%; Overall yield = 690.1 mg; |
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Procarbazine(CAS NO.671-16-9) has the Synonyms of Procarbazine; N-(1-Methylethyl)-4-((2-methylhydrazino)methyl)benzamide; 1-Methyl-2-(p-(isopropylcarbamoyl)benzyl)hydrazine; 2-(P-Isopropylcarbamoylbenzyl)-1-methylhydrazine; 4-((2-Methylhydrazino)methyl)-N-isopropylbenzamide; Benzamide, N-(1-methylethyl)-4-[(2-methylhydrazino)methyl]-; CB400-497; Ibenzmethyzin. It is an antineoplastic chemotherapy drug for the treatment of Hodgkin's lymphoma and certain brain cancers (such as Glioblastoma multiforme). It is a member of a group of medicines called alkylating agents. The drug is metabolized and activated in the liver. It also inhibits MAO thus increasing the effects of sympathomimetics, TCAs, and tyramine.
Physical properties about Procarbazine are: (1)ACD/LogP: 0.06; (2)ACD/LogD (pH 5.5): -2.34; (3)ACD/LogD (pH 7.4): -0.64; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 5.17; (8)#H bond acceptors: 4; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 5; (11)Index of Refraction: 1.529; (12)Molar Refractivity: 65.839 cm3; (13)Molar Volume: 213.619 cm3; (14)Polarizability: 26.101 10-24cm3; (15)Surface Tension: 37.8580017089844 dyne/cm; (16)Density: 1.036 g/cm3; (17)Flash Point: 148.864 °C; (18)Enthalpy of Vaporization: 63.328 kJ/mol; (19)Boiling Point: 384.589 °C at 760 mmHg
You can still convert the following datas into molecular structure:
(1)InChI=1S/C12H19N3O/c1-9(2)15-12(16)11-6-4-10(5-7-11)8-14-13-3/h4-7,9,13-14H,8H2,1-3H3,(H,15,16);
(2)InChIKey=CPTBDICYNRMXFX-UHFFFAOYSA-N;
(3)Smilesc1(C(NC(C)C)=O)ccc(CNNC)cc1;
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 614mg/kg (614mg/kg) | JNCI, Journal of the National Cancer Institute. Vol. 62, Pg. 911, 1979. | |
rat | LD50 | intraperitoneal | > 400mg/kg (400mg/kg) | Advances in Teratology. Vol. 3, Pg. 181, 1968. | |
rat | LD50 | unreported | 350mg/kg (350mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 363, 1970. |