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| CAS No.: | 68-41-7 |
|---|---|
| Name: | D-Cycloserine |
| Article Data: | 37 |
| Molecular Structure: | |
|
|
|
| Formula: | C3H6N2O2 |
| Molecular Weight: | 102.093 |
| Synonyms: | 3-Isoxazolidinone,4-amino-, (+)- (8CI);3-Isoxazolidinone, 4-amino-, (R)-;(+)-Cycloserine;(4R)-4-Amino-3-isoxazolidinone;(R)-4-Amino-3-isoxazolidinone;(R)-Cycloserine;Cyclo-D-serine;Cycloserine;D-4-Amino-3-isoxazolidinone;D-4-Amino-3-isoxazolidone;D-CS;Farmiserina;Micoserina;Miroseryn;NSC 154851;Novoserin;Orientomycin;Oxamycin;Seromycin;Tisomycin;Wasserina;D-Cycloserine; |
| EINECS: | 200-688-4 |
| Density: | 1.278 g/cm3 |
| Melting Point: | 147ºC |
| Boiling Point: | 267ºC |
| Solubility: | soluble in water |
| Appearance: | White to pale yellow cryst. powder |
| Hazard Symbols: |
 Xn
|
| Risk Codes: | 5-20 |
| Safety: | 38-36/37-24/25 |
| PSA: | 64.35000 |
| LogP: | -0.59580 |
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- 17136-54-8
Methyl (2R)-2-amino-3-chloropropionate hydrochloride
- 68-41-7
cycloserine
| Conditions | Yield |
|---|---|
| With hydrogenchloride; acetone oxime In methanol at 65℃; for 1h; Temperature; | 94.25% |
- 29491-80-3
methyl (2R)-2-amino-3-(aminooxy)propanoate
- 68-41-7
cycloserine
| Conditions | Yield |
|---|---|
| Stage #1: methyl (2R)-2-amino-3-(aminooxy)propanoate With sodium hydroxide In water at -5 - 0℃; for 3h; Stage #2: With acetic acid In water; isopropyl alcohol at -12 - -8℃; for 1h; pH=6.7 - 6.9; | 80% |
| Conditions | Yield |
|---|---|
| With hydroxylamine hydrochloride; sodium hydroxide In methanol; water at 0 - 20℃; for 5h; | A 66% B 27% |
| With hydroxylamine hydrochloride; sodium methylate In methanol; water at 0 - 20℃; for 9h; | A 39% B 48% |
- 72270-01-0
D-cycloserine-L-tartrate
- 68-41-7
cycloserine
| Conditions | Yield |
|---|---|
| With Amberlite IR-120 PLUS ion exchange resin (sodium form) In water Inert atmosphere; | 65% |
- 121362-14-9
D-2-amino-3-chloropropionic acid chloride hydrochloride
- 68-41-7
cycloserine
| Conditions | Yield |
|---|---|
| With hydroxylamine hydrochloride; sodium hydroxide In water; toluene at -5 - 30℃; pH=11 - 12; pH-value; | 58.1% |
- 120883-74-1
D-2-amino-3-chloropropionohydroxamic acid hydrochloride
- 68-41-7
cycloserine
| Conditions | Yield |
|---|---|
| With sodium hydroxide In water at 25℃; pH=11; Cooling; | 50% |
- 23628-35-5
3-chloro-D-alanine hydroxyamide
- 68-41-7
cycloserine
| Conditions | Yield |
|---|---|
| With water; triethylamine |
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Consensus Reports
Specification
The Cycloserine, with the CAS registry number 68-41-7 and EINECS registry number 200-688-4, has the systematic name of (4R)-4-amino-1,2-oxazolidin-3-one. It is a kind of white to pale crystal powder, and belongs to the following product categories: Variousamine; Miscellaneous Biochemicals; Chiral; Amines (Chiral); Chiral Building Blocks; Synthetic Organic Chemistry; Amino Acids; Glutamate receptor; Glutamate; Antibiotics. And the molecular formula of this chemical is C3H6N2O2. What's more, it should be stored at -20°C.
The physical properties of Cycloserine are as followings: (1)ACD/LogP: -2.988; (2)ACD/LogD (pH 5.5): -3.54; (3)ACD/LogD (pH 7.4): -3.00; (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): 1.00; (8)#H bond acceptors: 4; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.475; (12)Molar Refractivity: 22.472 cm3; (13)Molar Volume: 79.861 cm3; (14)Polarizability: 8.909 10-24cm3; (15)Surface Tension: 40.8849983215332 dyne/cm; (16)Density: 1.278 g/cm3
Preparation of Cycloserine: It can be synthesised by fomentation and direct synthesis technique. Fomentation need zymogen the Actinomyces laven-dulae, and the fermentation medium dextrin, glucose, starch, soybean powder, yeast powder, ammonium sulfate, ammonium nitrate, calcium carbonate, sodium chloride, magnesium sulfate, soybean oil and so on. Direct synthesis technique is a cyclization reaction between β-amino alanine ethyl ester dihydrochloride oxygen and KOH.
Uses of Cycloserine: It is an antibiotic effective against Mycobacterium tuberculosis, and usually used for the treatment of tuberculosis. It is also being trialed as an adjuvant to exposure therapy for anxiety disorders.
You should be cautious while dealing with this chemical. Heating may cause an explosion, and it is also harmful by inhalation. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and avoid contacting with skin and eyes.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C1NOC[C@H]1N
(2)InChI: InChI=1/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1
(3)InChIKey: DYDCUQKUCUHJBH-UWTATZPHBN
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| dog | LD50 | oral | > 2gm/kg (2000mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING | Antibiotics and Chemotherapy Vol. 6, Pg. 360, 1956. |
| dog | LDLo | subcutaneous | 2gm/kg (2000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: TREMOR GASTROINTESTINAL: NAUSEA OR VOMITING | Antibiotics and Chemotherapy Vol. 6, Pg. 708, 1956. |
| guinea pig | LD50 | oral | > 2gm/kg (2000mg/kg) | Antibiotics and Chemotherapy Vol. 6, Pg. 360, 1956. | |
| guinea pig | LD50 | subcutaneous | > 1gm/kg (1000mg/kg) | Antibiotics and Chemotherapy Vol. 6, Pg. 360, 1956. | |
| human | TDLo | oral | 560mg/kg/4W-I (560mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: WAKEFULNESS | Diseases of the Chest. Vol. 29, Pg. 241, 1956. |
| man | TDLo | unreported | 64mg/kg/4D-I (64mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: SLEEP | Antibiotics Annual. Vol. 3, Pg. 148, 1955/1956. |
| monkey | LDLo | subcutaneous | 4gm/kg (4000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: NAUSEA OR VOMITING BEHAVIORAL: ATAXIA | Antibiotics and Chemotherapy Vol. 6, Pg. 708, 1956. |
| mouse | LD50 | intraperitoneal | 180mg/kg (180mg/kg) | "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 238, 1967. | |
| mouse | LD50 | intravenous | 560mg/kg (560mg/kg) | Yakkyoku. Pharmacy. Vol. 31, Pg. 1085, 1980. | |
| mouse | LD50 | oral | 5290mg/kg (5290mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA | Antibiotics and Chemotherapy Vol. 6, Pg. 360, 1956. |
| mouse | LD50 | subcutaneous | 1400mg/kg (1400mg/kg) | Yakkyoku. Pharmacy. Vol. 31, Pg. 1085, 1980. | |
| rabbit | LD | oral | > 2gm/kg (2000mg/kg) | Antibiotics and Chemotherapy Vol. 6, Pg. 382, 1956. | |
| rat | LD50 | oral | > 5gm/kg (5000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Antibiotics and Chemotherapy Vol. 6, Pg. 360, 1956. |
| rat | LD50 | subcutaneous | > 3gm/kg (3000mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Antibiotics and Chemotherapy Vol. 6, Pg. 360, 1956. |
| women | TDLo | oral | 60mg/kg (60mg/kg) | BEHAVIORAL: COMA | British Medical Journal. Vol. 1, Pg. 907, 1965. |
| women | TDLo | oral | 5gm/kg/71W-I (5000mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES | Rinsho Shinkeigaku. Clinical Neurology. Vol. 7, Pg. 357, 1967. |
| women | TDLo | unreported | 40mg/kg/2D-I (40mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" | Tubercle. Vol. 38, Pg. 297, 1957. |