Methylazoxymethanol | 590-96-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: Methylazoxymethanol
• 英文别名: (Z)-hydroxymethylimino-methyl-oxidoazanium
• CAS: 590-96-5
• 化学式: C2H6N2O2
• 分子量: 90.08
• InChiKey: BJNBRIBHKLJMAG-ARJAWSKDSA-N

物化性质

• 沸点：
  167.26°C (rough estimate)
• 密度：
  1.3348 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  61.3
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

代谢

甲基氧化吗啡醇是酶马肝醇脱氢酶的底物。甲基氧化吗啡醇的醛形式是一种非常不稳定的化合物，它会迅速释放碳正离子。

METHYLAZOXYMETHANOL IS A SUBSTRATE FOR THE ENZYME HORSE LIVER ALCOHOL DEHYDROGENASE. THE ALDEHYDIC FORM OF METHYLAZOXYMETHANOL IS A VERY UNSTABLE CMPD WHICH RAPIDLY RELEASES CARBONIUM IONS.

来源:Hazardous Substances Data Bank (HSDB)

代谢

1,2-二甲基肼（DMH）在隔离灌注的大鼠肝脏中被高度代谢。灌注1小时后，培养基中DMH及其代谢物的中位量分别为：DMH 16%，偶氮甲烷3%，偶氮氧甲烷42%，甲基偶氮氧甲醇30%，占给定剂量的比例。

1,2-DIMETHYLHYDRAZINE (DMH) IS HIGHLY METABOLIZED BY ISOLATED PERFUSED RAT LIVER. AFTER 1 HR OF PERFUSION, THE MEDIAN AMT OF DMH AND ITS METABOLITES IN THE MEDIUM WERE: DMH 16, AZOMETHAN 3, AZOXYMETHANE 42, AND METHYLAZOXYMETHANOL 30% OF THE GIVEN DOSE.

来源:Hazardous Substances Data Bank (HSDB)

代谢

NDDO半经验分子轨道研究方法被用于模拟提出的非酶代谢途径，将甲基氧化甲烷醇分解为甲基重氮基。

THE NDDO SEMIEMPIRICAL MOLECULAR ORBITAL STUDY METHOD WAS USED TO MODEL PROPOSED NONENZYME METABOLIC PATHWAYS FOR THE DECOMP OF METHYLAZOXYMETHANOL TO METHYLDIAZONIUM.

来源:Hazardous Substances Data Bank (HSDB)

代谢

NDDO半经验分子轨道研究方法被用于描述甲基氧化甲酰胺（MAM）及其代谢物与DNA亲核碱基位点的反应性。

THE NDDO SEMIEMPIRICAL MOLECULAR ORBITAL STUDY METHOD WAS USED TO CHARACTERIZE THE REACTIVITIES OF METHYLAZOXYMETHANOL (MAM) AND ITS METABOLITES WITH DNA NUCLEOPHILIC BASE SITES.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在大鼠口服给药后，苏铁苷被肠道菌群中的β-葡萄糖苷酶分解，形成甲基氧化甲醇。在新生小鼠和大鼠的皮下组织中也会发生酶促水解，生成甲基氧化甲醇，这些组织在出生后早期含有葡萄糖苷酶，这种酶在第14至25天后消失。

FOLLOWING...ORAL ADMIN TO RATS, CYCASIN IS SPLIT BY BETA-GLUCOSIDASE OF BACTERIAL FLORA TO FORM METHYLAZOXYMETHANOL. ENZYMATIC HYDROLYSIS TO METHYLAZOXYMETHANOL ALSO OCCURS IN SUBCUTANEOUS TISSUES OF NEWBORN MICE & RATS, WHICH IN EARLY POSTNATAL PERIOD CONTAIN GLUCOSIDASE THAT DISAPPEARS AFTER 14TH-25TH DAY OF LIFE.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

没有关于人类的数据。动物中有充分的致癌性证据。总体评估：2B组：该物质可能对人类致癌。/甲基氧化甲基醇及其醋酸盐的数据合并/

No data are available in humans. Sufficient evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 2B: The agent is possibly carcinogenic to humans. /Data lumped for methylazoxymethanol and its acetate/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 副作用

神经毒素 - 其他中枢神经系统神经毒素 生殖毒素 - 对生殖系统有毒的化学物质，包括后代缺陷以及损伤男性或女性生殖功能。生殖毒性包括发育效应。参见生殖毒性风险评估指南。 国际癌症研究机构致癌物 - 第3类：化学物质无法被国际癌症研究机构分类。

Neurotoxin - Other CNS neurotoxin Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment. IARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

毒理性

• 相互作用

膳食叔丁基对羟基茴香醚对甲基偶氮氧基甲醇处理的小肠粘膜具有增殖作用。

DIETARY BUTYLATED HYDROXYANISOLE HAS A PROLIFERATING EFFECT ON METHYLAZOXYMETHANOL TREATED COLONIC MUCOSA.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 医疗监测

对于"致癌物"的预防措施：每当需要进行医疗监测时，尤其是在暴露于致癌物的情况下，应就.../细胞遗传学和其他/可能变得有用或必须进行的测试做出特别决定。/化学致癌物/

PRECAUTIONS FOR "CARCINOGENS": Whenever medical surveillance is indicated, in particular when exposure to a carcinogen has occurred, ad hoc decisions should be taken concerning ... /cytogenetic and/or other/ tests that might become useful or mandatory. /Chemical Carcinogens/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 非人类毒性摘录

在怀孕的第8天给雌性仓鼠注射20-23毫克/千克体重的甲基氧化甲烷醇后，观察到胎儿神经系统的畸形。怀孕第12天时，将雌性仓鼠牺牲以检查胎儿。通过用β-葡萄糖苷酶处理苏铁苷来制备的甲基氧化甲烷醇，在喂食给Canton S品系果蝇雄性时被发现能诱导性连锁隐性致死突变。在摄入0.09或0.1微克/每只果蝇后观察到强烈的致突变效果，但是摄入0.76或9.3微克/每只果蝇的苏铁苷并没有致突变作用。从结晶苏铁苷衍生出的甲基氧化甲烷醇在沙门氏菌属伤寒杆菌中诱导了逆向突变，尽管原始化合物CMPD是无效的。

MALFORMATIONS OF NERVOUS SYSTEM WERE OBSERVED IN FETUSES OF FEMALE HAMSTERS INJECTED WITH 20-23 MG/KG BODY WT METHYLAZOXYMETHANOL ON 8TH DAY OF PREGNANCY. FEMALES WERE SACRIFICED AT 12TH DAY OF PREGNANCY FOR EXAMINATION OF FETUSES. METHYLAZOXYMETHANOL, PREPARED BY TREATING CYCASIN WITH BETA-GLUCOSIDASE, WAS FOUND TO INDUCE SEX-LINKED RECESSIVE LETHALS WHEN FED TO DROSOPHILA MELANOGASTER MALES OF CANTON S STRAIN. STRONG MUTAGENIC EFFECTS WERE OBSERVED AFTER UPTAKE OF 0.09 OR 0.1 UG...PER FLY, BUT UPTAKES OF 0.76 OR 9.3 UG CYCASIN PER FLY WERE NOT MUTAGENIC. METHYLAZOXYMETHANOL DERIVED FROM CRYSTALLINE CYCASIN INDUCED REVERSE MUTATIONS IN SALMONELLA TYPHIMURIUM, ALTHOUGH PARENT CMPD WAS INACTIVE.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

.../CROSSES/ 在大鼠和仓鼠中穿过胎盘。

.../CROSSES/ THE PLACENTA IN RATS & HAMSTERS.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

分泌到乳汁中。

...EXCRETED IN MILK DURING LACTATION.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  6.1(b)

反应信息

• 作为反应物：
  描述：

  Methylazoxymethanol 、 UDP-glucose 生成 beta-D-Glucosyloxyazoxymethane 、 氢(+1)阳离子 、 UDP
  参考文献：
  名称：

  摘要：

  DOI：