左旋安非他命

左旋安非他命
系统名
(2R)-1-Phenylpropan-2-amine[1]
识别
CAS号 156-34-3  checkY
PubChem 32893
ChemSpider 30477
SMILES
 
  • C[C@@H](N)Cc1ccccc1
Beilstein 2432739
Gmelin 1125855
EINECS 205-850-8
ChEBI 42724
IUPHAR配体 2146
性质
化学式 C9H13N
摩尔质量 135.21 g·mol−1
log P 1.789
药理学
药品分级
给药途径 口服给药(作为阿得拉的一部分),Evekeo,以及通用硫酸苯丙胺[2][3])
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

左旋安非他命(英語:Levoamphetamine,也称levamfetamineINN[4](R)-amphetamine[4]L-amphetamine)是一种中枢神经系统刺激剂,可提升清醒度、增强注意力,伴有食欲不振和疲倦。目前在某些国家中,含有左旋安非他命的药物被认为能够治疗注意力不足過動症(ADHD)、肥胖症發作性嗜睡病

化学

左旋安非他命是苯丙胺分子的左旋立体异构体。外消旋苯丙胺含有两种光学异构体,右旋安非他命和左旋安非他命。[5]

制剂

外消旋安非他命

第一个获得专利的安非他明品牌Benzedrine是苯丙胺两种对映异构体(左旋安非他明和右旋安非他明)的游离碱或硫酸盐的外消旋混合物,于1934年在美国引入,作为治疗鼻塞的吸入剂。[2]后来人们意识到安非他明对映体可以治疗肥胖症發作性嗜睡病ADHD[2][3][6]由于右旋对映异构体(以迪西卷的形式出售)具有更大的中枢神经系统作用,Benzedrine品牌的处方下降并最终停止使用。[7]然而,在2012年,外消旋安非他明硫酸盐以Evekeo品牌名称被重新引入。[3]

阿得拉尔是一种含有25%左旋安非他明盐的苯丙胺药物。[5]

Evekeo

Evekeo英语EvekeoFDA批准的药物,含有外消旋苯丙胺硫酸盐(即50%左旋安非他明硫酸盐和50%右旋安非他明硫酸盐)。[8]它被批准用于治疗發作性嗜睡病ADHD和外源性肥胖症[8]

参见

参考资料

  1. ^ Amphetamine - PubChem Public Chemical Project. The PubChem Project. USA: National Center for Biotechnology Information. Descriptors Computed from Structure. 2005-08-08 [2011-09-26]. (原始内容存档于2013-06-03). 
  2. ^ 2.0 2.1 2.2 Heal DJ, Smith SL, Gosden J, Nutt DJ. Amphetamine, past and present – a pharmacological and clinical perspective. J. Psychopharmacol. June 2013, 27 (6): 479–496. PMC 3666194可免费查阅. PMID 23539642. doi:10.1177/0269881113482532. 
  3. ^ 3.0 3.1 3.2 Evekeo prescribing information (PDF). Arbor Pharmaceuticals LLC: 1–2. April 2014 [2015-08-11]. (原始内容存档 (PDF)于2016-03-04). 
  4. ^ 4.0 4.1 R(-)amphetamine. IUPHAR/BPS Guide to PHARMACOLOGY. [2016-03-30]. (原始内容存档于2020-09-20). 
  5. ^ 5.0 5.1 Adderall XR Prescribing Information (PDF). United States Food and Drug Administration. December 2013 [30 December 2013]. (原始内容存档 (PDF)于2013-12-30). 
  6. ^ Evekeo. United States Food and Drug Administration. [11 August 2015]. (原始内容存档于2021-03-08). 
  7. ^ Benzedrine. United States Food and Drug Administration. [4 September 2015]. (原始内容存档于2021-01-19). 
  8. ^ 8.0 8.1 Evekeo Prescribing Information (PDF). Evekeo (Arbor Pharmaceuticals, LLC). December 2016 [6 December 2016]. (原始内容存档 (PDF)于2016-03-04). 

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