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盐酸脱氧麻黄碱 | 51-57-0

中文名称
盐酸脱氧麻黄碱
中文别名
去氧麻黄碱盐酸盐;脱氧麻黄碱盐酸盐;盐酸司维拉姆
英文名称
S-methamphetamine hydrochloride
英文别名
methamphetamine hydrochloride;methamphetamine;d-methamphetamine hydrochloride;methylamphetamine hydrochloride;methamphetamine·HCl;Metamphetamine hydrochloride;Desoxyn;hydron;(2S)-N-methyl-1-phenylpropan-2-amine;chloride
盐酸脱氧麻黄碱化学式
CAS
51-57-0
化学式
C10H15N*ClH
mdl
——
分子量
185.697
InChiKey
TWXDDNPPQUTEOV-FVGYRXGTSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    2.26
  • 重原子数:
    12
  • 可旋转键数:
    3
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.4
  • 拓扑面积:
    12
  • 氢给体数:
    2
  • 氢受体数:
    1

ADMET

毒理性
  • 在妊娠和哺乳期间的影响
◉ 哺乳期使用概述:由于没有关于哺乳期将甲基苯丙胺作为治疗剂的经验发表,可能更倾向于选择其他药物,特别是在哺乳新生儿或早产儿时。一位专家建议,不应在哺乳母亲中作为治疗用途使用安非他命。 哺乳母亲不应将甲基苯丙胺作为娱乐性药物使用,因为它可能会影响她们的判断力和照顾孩子的能力。在哺乳母亲滥用甲基苯丙胺后,甲基苯丙胺及其代谢物安非他命在母乳和婴儿血清中可被检测到。然而,由于在哺乳母亲身上进行娱乐性甲基苯丙胺的给药存在伦理考虑,这些数据来自随机收集而不是控制研究。其他需要考虑的因素包括哺乳婴儿可能出现的阳性尿检,这可能具有法律影响,以及街头毒品可能存在其他有害杂质的可能性。通常不鼓励积极滥用安非他命的哺乳母亲进行哺乳。在哺乳期间滥用甲基苯丙胺的母亲,建议在最后一次使用后48至100小时不进行哺乳,尽管许多母亲在最后一次使用后平均72小时母乳中就检测不到甲基苯丙胺。有人建议,在母亲安非他命尿检阴性24小时后可以恢复哺乳。 ◉ 对哺乳婴儿的影响:一名两个月大的婴儿,其母亲通过鼻腔吸入娱乐性街头甲基苯丙胺后,在少量哺乳和摄入120至180毫升配方奶后8小时被发现死亡。尸检时婴儿血清中甲基苯丙胺浓度为39微克/升。尽管婴儿的母亲因在哺乳期间使用甲基苯丙胺而被判定为危害儿童安全,但由于婴儿血清中甲基苯丙胺浓度较低以及母亲据称哺乳次数较少,甲基苯丙胺在婴儿死亡中的作用受到了质疑。 南澳大利亚政府病理学家报告了一名与母亲同睡的哺乳婴儿的死亡。尸检时在婴儿体内发现了“显著”浓度的甲基苯丙胺,认为母乳中的药物可能是导致死亡的一个潜在因素。这些作者还报告说,在之前12个月以下婴儿的死亡案例中,检测到的甲基苯丙胺及其代谢物安非他命可能部分是通过母乳获得的。新西兰政府病理学家也确认了他们国家类似的发现。 ◉ 对泌乳和母乳的影响:给6名受试者(4名男性和2名女性)单次口服0.2毫克/公斤,最大剂量为17.5毫克的d-甲基苯丙胺。在给药后300分钟内,血清催乳素浓度没有变化。 在相同作者的两篇论文中,研究了20名生理性高催乳素血症的正常女性,这些女性在分娩后第2或第3天进行研究。其中8人静脉注射了7.5毫克右旋安非他命,6人静脉注射了15毫克,6人作为对照组静脉注射了生理盐水。7.5毫克剂量使血清催乳素下降了25至32%,与对照组相比差异无统计学意义。15毫克剂量在输注后一段时间显著降低了血清催乳素30至37%。没有提供对泌乳量的评估。作者还引用了另一项研究的数据,显示产后女性口服20毫克右旋安非他命可使血清催乳素持续抑制40%。 一项研究比较了31名甲基苯丙胺依赖受试者和23名非依赖受试者。甲基苯丙胺依赖受试者在戒断后第2天和第30天的血清催乳素浓度升高。这种升高在女性中比男性更明显。在已建立泌乳的母亲中,母体催乳素水平可能不会影响她的哺乳能力。 在一项回顾性澳大利亚研究中,与滥用其他药物的母亲相比,怀孕期间使用静脉注射安非他命的母亲的婴儿在出院时更不可能接受哺乳(27%对42%)。这种差异的原因尚未确定。 一项前瞻性、多中心研究跟踪了产前使用甲基苯丙胺的母亲(n=204)和未使用的母亲(n=208)。暴露于甲基苯丙胺的婴儿表现出吸吮力差、过度吸吮和比未暴露婴儿更多的颤抖。使用甲基苯丙胺的母亲在出院时哺乳婴儿的可能性较低(38%),而未使用甲基苯丙胺的母亲则为76%。
◉ Summary of Use during Lactation:Because there is no published experience with methamphetamine as a therapeutic agent during breastfeeding, an alternate drug may be preferred, especially while nursing a newborn or preterm infant. One expert recommends that amphetamines not be used therapeutically in nursing mothers. Methamphetamine should not be used as a recreational drug by nursing mothers because it may impair their judgment and childcare abilities. Methamphetamine and its metabolite, amphetamine, are detectable in breastmilk and infant's serum after abuse of methamphetamine by nursing mothers. However, these data are from random collections rather than controlled studies because of ethical considerations in administering recreational methamphetamine to nursing mothers. Other factors to consider are the possibility of positive urine tests in breastfed infants which might have legal implications, and the possibility of other harmful contaminants in street drugs. Breastfeeding is generally discouraged in mothers who are actively abusing amphetamines. In mothers who abuse methamphetamine while nursing, withholding breastfeeding for 48 to 100 hours after the maternal use been recommended, although in many mothers methamphetamine is undetectable in breastmilk after an average of 72 hours from the last use. It has been suggested that breastfeeding can be reinstated 24 hours after a negative maternal urine screen for amphetamines. ◉ Effects in Breastfed Infants:A 2-month-old infant whose mother used illicit street methamphetamine recreationally by nasal inhalation was found dead 8 hours after a small amount of breastfeeding and ingestion of 120 to 180 mL of formula. The infant's serum methamphetamine concentration on autopsy was 39 mcg/L. Although the infant's mother was convicted of child endangerment for the use of methamphetamine during breastfeeding, the role that methamphetamine played in the infant's death has been questioned because of the low infant serum methamphetamine concentration and the mother's alleged minimal breastfeeding. South Australian government pathologists reported the death of a breastfed infant who was co-sleeping with its mother. Methamphetamine was found in a “significant” concentration in the infant on autopsy and the drug in breastmilk was thought to be potentially contributory to the death. These authors also reported that in prior deaths of infants under 12 months of age, detectable methamphetamine and its metabolite, amphetamine, may have been partially obtained via breastmilk. Pathologists from the New Zealand government confirmed similar findings in their country. ◉ Effects on Lactation and Breastmilk:A single oral dose of 0.2 mg/kg to a maximum of 17.5 mg of d-methamphetamine was given to 6 subjects (4 male and 2 female). Serum prolactin concentrations were unchanged over a period of 300 minutes after the dose. In 2 papers by the same authors, 20 women with normal physiologic hyperprolactinemia were studied on days 2 or 3 postpartum. Eight received dextroamphetamine 7.5 mg intravenously, 6 received 15 mg intravenously and 6 who served as controls received intravenous saline. The 7.5 mg dose reduced serum prolactin by 25 to 32% compared to control, but the difference was not statistically significant. The 15 mg dose significantly decreased serum prolactin by 30 to 37% at times after the infusion. No assessment of milk production was presented. The authors also quoted data from another study showing that a 20 mg oral dose of dextroamphetamine produced a sustained suppression of serum prolactin by 40% in postpartum women. A study compared 31 methamphetamine-dependent subject to 23 non-dependent subjects. The serum prolactin concentrations in the methamphetamine-dependent subjects were elevated at days 2 and 30 of abstinence. The elevation was greater in women than in men. The maternal prolactin level in a mother with established lactation may not affect her ability to breastfeed. In a retrospective Australian study, mothers who used intravenous amphetamines during pregnancy were less likely to be breastfeeding their newborn infants at discharge than mothers who abused other drugs (27% vs 42%). The cause of this difference was not determined. A prospective, multicenter study followed mothers who used methamphetamine prenatally (n = 204) to those who did not (n = 208). Infants exposed to methamphetamine exhibited poor suck, excessive suck and more jitteriness compared to nonexposed infants. Mothers who used methamphetamine were less likely to breastfeed their infants (38%) at hospital discharge than those who did not use methamphetamine (76%).
来源:Drugs and Lactation Database (LactMed)
毒理性
  • 在妊娠和哺乳期间的影响
哺乳期使用总结:在用于医疗指征的剂量下,有证据表明右旋安非他命可能不会对哺乳婴儿产生不利影响。右旋安非他命在乳汁中对婴儿神经发育的影响尚未得到充分研究。高剂量的右旋安非他命可能会干扰乳汁生产,特别是在哺乳尚未建立的妇女中。截至修订日期,没有找到关于在滥用安非他命期间哺乳安全性的已发布信息。一位专家建议哺乳母亲不应将安非他命用作治疗。 对哺乳婴儿的影响:1973年一份通讯的作者报告了来自药品制造商的个人通讯,称在103名接受右旋安非他命(剂量未指定)治疗产后抑郁症的哺乳母亲中,没有婴儿出现任何刺激或失眠的证据。 四名平均产后5.5个月(范围3.3至10个月)的母亲正在服用右旋安非他命,平均剂量为每天18毫克(范围15至45毫克,每天分2至4次服用)治疗注意力缺陷多动障碍。她们的婴儿自出生以来一直在哺乳(程度未说明)。这些婴儿的体重都处于他们年龄的10至75百分位之间,发育正常,根据儿科医生的说法,没有不良反应。其中2名婴儿的丹佛发展年龄分别为正常的100%和117%。 对哺乳和乳汁的影响:在两篇同一作者的研究论文中,研究了20名生理性高催乳素血症正常的妇女,在产后第2或第3天。其中8人接受了7.5毫克静脉注射右旋安非他命,6人接受了15毫克静脉注射,6人作为对照组接受了静脉注射生理盐水。7.5毫克剂量使血清催乳素降低了25至32%,与对照组相比,但差异无统计学意义。15毫克剂量在输注后显著降低了血清催乳素30至37%。没有提出乳汁生产的评估。作者还引用了另一项研究的数据,显示20毫克口服剂量的右旋安非他命在产后妇女中产生了40%的血清催乳素持续抑制。在已建立哺乳的母亲中,母体催乳素水平可能不会影响她的哺乳能力。 在一项回顾性澳大利亚研究中,与滥用其他药物的母亲相比,在怀孕期间使用静脉注射安非他命的母亲在出院时哺乳新生儿的可能性较小(27%对42%)。这种差异的原因尚未确定。
◉ Summary of Use during Lactation:In dosages prescribed for medical indications, some evidence indicates that dextroamphetamine might not affect nursing infants adversely. The effect of dextroamphetamine in milk on the neurological development of the infant has not been well studied. It is possible that large dosages of dextroamphetamine might interfere with milk production, especially in women whose lactation is not well established. Relevant published information was not found as of the revision date on the safety of breastfeeding during amphetamine abuse. One expert recommends that amphetamines not be used therapeutically in nursing mothers. ◉ Effects in Breastfed Infants:The author of a 1973 newsletter reported a personal communication from the drug manufacturer which stated that of 103 nursing mothers treated with dextroamphetamine (dosage unspecified) for postpartum depression, no infant showed any evidence of stimulation or insomnia. Four mothers averaging 5.5 months postpartum (range 3.3 to 10 months) were taking dextroamphetamine in an average dosage of 18 mg daily (range 15 to 45 mg daily in 2 to 4 divided doses) for attention deficit hyperactivity disorder. Their infants had been breastfed (extent not stated) since birth. The infants all had weights between the 10th and 75th percentiles for their age, normal progress, and no adverse effects according to their pediatricians. Denver developmental ages for 2 of the infants were 100% and 117% of normal. ◉ Effects on Lactation and Breastmilk:In 2 papers by the same authors, 20 women with normal physiologic hyperprolactinemia were studied on days 2 or 3 postpartum. Eight received dextroamphetamine 7.5 mg intravenously, 6 received 15 mg intravenously and 6 who served as controls received intravenous saline. The 7.5 mg dose reduced serum prolactin by 25 to 32% compared to control, but the difference was not statistically significant. The 15 mg dose significantly decreased serum prolactin by 30 to 37% at times after the infusion. No assessment of milk production was presented. The authors also quoted data from another study showing that a 20 mg oral dose of dextroamphetamine produced a sustained suppression of serum prolactin by 40% in postpartum women. The maternal prolactin level in a mother with established lactation may not affect her ability to breastfeed. In a retrospective Australian study, mothers who used intravenous amphetamines during pregnancy were less likely to be breastfeeding their newborn infants at discharge than mothers who abused other drugs (27% vs 42%). The cause of this difference was not determined.
来源:Drugs and Lactation Database (LactMed)

反应信息

  • 作为反应物:
    描述:
    参考文献:
    名称:
    Amphetamine derivatives and protein and polypeptide amphetamine
    摘要:
    本发明涉及一种新型苯丙胺衍生物,用于与抗原(蛋白质或多肽)共价结合,以制备针对苯丙胺及其代谢产物的抗体或受体。所得的新型抗原可用于使用标准方法制备抗体或受体。一旦生成,这些抗体或受体以及与蛋白质、多肽或标记物共价结合的新型衍生物可在免疫分析过程中使用。
    公开号:
    US05470997A1
  • 作为产物:
    描述:
    在 palladium on barium sulfate 作用下, 以 为溶剂, 反应 4.0h, 以75%的产率得到盐酸脱氧麻黄碱
    参考文献:
    名称:
    通过NMR光谱分析麻黄碱和甲基苯丙胺的氘特征分布。
    摘要:
    我们建立了一种通过2H NMR定量分析l-麻黄碱/ HCl,d-伪麻黄碱/ HCl和甲基苯丙胺/ HCl的苯基,次甲基,苄基,N-甲基和甲基上的氘含量(D / H)的方法光谱学。比较三种方法(化学合成,半化学合成和生物合成)制得的左旋麻黄碱/ HCl和d-伪麻黄碱/ HCl的5个位置特异性D / H值,发现化学合成的麻黄碱和半合成的麻黄碱具有很高的比分布。与其他位置相比,次甲基和苄基位置上的氘。根据在这两个位置的D / H值对日本缉获的几种甲基苯丙胺样品进行的分类清楚地表明,甲基苯丙胺样品是从麻黄植物或半合成麻黄碱中提取的麻黄碱合成的,而不是从合成麻黄碱中提取的。这种同位素比分析方法应有助于追踪东南亚缉获的甲基苯丙胺的起源。
    DOI:
    10.1021/ac701639j
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文献信息

  • [EN] PROCESSES USEFUL FOR THE SYNTHESIS OF (R)-1-{2-[4'-(3-METHOXYPROPANE-1-SULFONYL)-BIPHENYL-4-YL]-ETHYL}-2-METHYL-PYRROLIDINE<br/>[FR] PROCÉDÉS UTILES POUR LA SYNTHÈSE DE LA (R)-1-{2-[4'-(3-MÉTHOXYPROPANE-1-SULFONYL)-BIPHÉNYL-4-YL]-ÉTHYL}-2-MÉTHYL-PYRROLIDINE
    申请人:ARENA PHARM INC
    公开号:WO2009128907A1
    公开(公告)日:2009-10-22
    Processes useful for making a pharmaceutically useful compound according to Formula (I), forms of such a compound, and intermediates useful in such processes are described.
    根据公式(I)制备药用化合物的有用过程,以及该化合物的形式和在这些过程中有用的中间体被描述。
  • [EN] SUBSTITUTED PIPERIDINE COMPOUND AND USE THEREOF<br/>[FR] COMPOSÉ DE PIPÉRIDINE SUBSTITUÉE ET SON UTILISATION
    申请人:TAKEDA PHARMACEUTICALS CO
    公开号:WO2017135306A1
    公开(公告)日:2017-08-10
    Provided is a substituted piperidine compound having an orexin type 2 receptor agonist activity. A compound represented by the formula (I): wherein each symbol is as described in the DESCRIPTION, or a salt thereof has an orexin type 2 receptor agonist activity, and is useful as a prophylactic or therapeutic agent for narcolepsy.
    提供的是一种替代哌啶化合物,具有促进俐克脑肽2型受体激动剂活性。公式(I)所代表的化合物:其中每个符号如描述中所述,或其盐具有促进俐克脑肽2型受体激动剂活性,并且可用作嗜睡症的预防或治疗药物。
  • Novel Bicyclic Pyridinones
    申请人:Pettersson Martin Youngjin
    公开号:US20120252758A1
    公开(公告)日:2012-10-04
    Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula I as defined herein. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.
    所述化合物及其药用可接受的盐被披露,其中所述化合物具有如本文所定义的Formula I的结构。相应的药物组合物、治疗方法、合成方法和中间体也被披露。
  • HETEROCYCLIC COMPOUND AND USE THEREOF
    申请人:Takeda Pharmaceutical Company Limited
    公开号:US20210198240A1
    公开(公告)日:2021-07-01
    The present invention provides a heterocyclic compound having an orexin type 2 receptor agonist activity. A compound represented by the formula (I): wherein each symbol is as described in the specification, or a salt thereof has an orexin type 2 receptor agonist activity, and is useful as an agent for the prophylaxis or treatment of narcolepsy.
    本发明提供了一种具有orexin类型2受体激动剂活性的杂环化合物。 表示为公式(I)的化合物: 其中每个符号如说明书中所述,或其盐具有orexin类型2受体激动剂活性,并且可用作预防或治疗发作性嗜睡症的药剂。
  • [EN] DEUTERATED MORPHINAN COMPOUNDS FOR USE IN TREATING AGITATION<br/>[FR] COMPOSÉS DE MORPHINANE DEUTÉRÉ POUR LE TRAITEMENT DE L'AGITATION
    申请人:CONCERT PHARMACEUTICALS INC
    公开号:WO2017020014A1
    公开(公告)日:2017-02-02
    This invention relates to methods of treating agitation comprising administering a morphinan compound or a pharmaceutically acceptable salt thereof. This invention also provides the use in methods of treating agitation and related disorders with such a morphinan compound in combination with quinidine, or pharmaceutically acceptable salt of either or both thereof.
    这项发明涉及治疗激动的方法,包括给予吗啡喃化合物或其药用可接受的盐。此发明还提供了在治疗激动和相关障碍的方法中使用这种吗啡喃化合物与奎尼丁或两者的药用可接受的盐的组合。
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表征谱图

  • 氢谱
    1HNMR
  • 质谱
    MS
  • 碳谱
    13CNMR
  • 红外
    IR
  • 拉曼
    Raman
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ir
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  • 峰位数据
  • 峰位匹配
  • 表征信息
Shift(ppm)
Intensity
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Assign
Shift(ppm)
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测试频率
样品用量
溶剂
溶剂用量
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同类化合物

(βS)-β-氨基-4-(4-羟基苯氧基)-3,5-二碘苯甲丙醇 (S)-(-)-7'-〔4(S)-(苄基)恶唑-2-基]-7-二(3,5-二-叔丁基苯基)膦基-2,2',3,3'-四氢-1,1-螺二氢茚 (S)-盐酸沙丁胺醇 (S)-3-(叔丁基)-4-(2,6-二甲氧基苯基)-2,3-二氢苯并[d][1,3]氧磷杂环戊二烯 (S)-2,2'-双[双(3,5-三氟甲基苯基)膦基]-4,4',6,6'-四甲氧基联苯 (S)-1-[3,5-双(三氟甲基)苯基]-3-[1-(二甲基氨基)-3-甲基丁烷-2-基]硫脲 (R)富马酸托特罗定 (R)-(-)-盐酸尼古地平 (R)-(+)-7-双(3,5-二叔丁基苯基)膦基7''-[((6-甲基吡啶-2-基甲基)氨基]-2,2'',3,3''-四氢-1,1''-螺双茚满 (R)-3-(叔丁基)-4-(2,6-二苯氧基苯基)-2,3-二氢苯并[d][1,3]氧杂磷杂环戊烯 (R)-2-[((二苯基膦基)甲基]吡咯烷 (N-(4-甲氧基苯基)-N-甲基-3-(1-哌啶基)丙-2-烯酰胺) (5-溴-2-羟基苯基)-4-氯苯甲酮 (5-溴-2-氯苯基)(4-羟基苯基)甲酮 (5-氧代-3-苯基-2,5-二氢-1,2,3,4-oxatriazol-3-鎓) (4S,5R)-4-甲基-5-苯基-1,2,3-氧代噻唑烷-2,2-二氧化物-3-羧酸叔丁酯 (4-溴苯基)-[2-氟-4-[6-[甲基(丙-2-烯基)氨基]己氧基]苯基]甲酮 (4-丁氧基苯甲基)三苯基溴化磷 (3aR,8aR)-(-)-4,4,8,8-四(3,5-二甲基苯基)四氢-2,2-二甲基-6-苯基-1,3-二氧戊环[4,5-e]二恶唑磷 (2Z)-3-[[(4-氯苯基)氨基]-2-氰基丙烯酸乙酯 (2S,3S,5S)-5-(叔丁氧基甲酰氨基)-2-(N-5-噻唑基-甲氧羰基)氨基-1,6-二苯基-3-羟基己烷 (2S,2''S,3S,3''S)-3,3''-二叔丁基-4,4''-双(2,6-二甲氧基苯基)-2,2'',3,3''-四氢-2,2''-联苯并[d][1,3]氧杂磷杂戊环 (2S)-(-)-2-{[[[[3,5-双(氟代甲基)苯基]氨基]硫代甲基]氨基}-N-(二苯基甲基)-N,3,3-三甲基丁酰胺 (2S)-2-[[[[[[((1R,2R)-2-氨基环己基]氨基]硫代甲基]氨基]-N-(二苯甲基)-N,3,3-三甲基丁酰胺 (2-硝基苯基)磷酸三酰胺 (2,6-二氯苯基)乙酰氯 (2,3-二甲氧基-5-甲基苯基)硼酸 (1S,2S,3S,5S)-5-叠氮基-3-(苯基甲氧基)-2-[(苯基甲氧基)甲基]环戊醇 (1-(4-氟苯基)环丙基)甲胺盐酸盐 (1-(3-溴苯基)环丁基)甲胺盐酸盐 (1-(2-氯苯基)环丁基)甲胺盐酸盐 (1-(2-氟苯基)环丙基)甲胺盐酸盐 (-)-去甲基西布曲明 龙胆酸钠 龙胆酸叔丁酯 龙胆酸 龙胆紫 龙胆紫 齐达帕胺 齐诺康唑 齐洛呋胺 齐墩果-12-烯[2,3-c][1,2,5]恶二唑-28-酸苯甲酯 齐培丙醇 齐咪苯 齐仑太尔 黑染料 黄酮,5-氨基-6-羟基-(5CI) 黄酮,6-氨基-3-羟基-(6CI) 黄蜡,合成物 黄草灵钾盐