左旋甲基苯丙胺

左旋甲基苯丙胺
临床资料
给药途径	医用 :吸入(鼻腔); 娱乐用 :口服静脉注射, insufflation,吸入栓剂
法律规范状态
法律规范	加：Schedule I; 德：Anlage II; 英：Class A; 美：Schedule II（英语：Controlled Substances Act#Schedule II drugs）;特定配方为OTC; UN：Psychotropic Schedule II;
药物动力学数据
药物代谢	肝脏
排泄途径	肾
识别信息
	IUPAC命名法 (R)-N-methyl-1-phenyl-propan-2-amine; ;
CAS号	33817-09-3
PubChem CID	36604;
ChemSpider	33634 ;
UNII	44RAL3456C;
KEGG	D02291 ;
CompTox Dashboard（英语：CompTox Chemicals Dashboard） (EPA)	DTXSID30187474 ;
ECHA InfoCard	100.046.974
化学信息
化学式	C10H15N
摩尔质量	149.2
3D模型（JSmol（英语：JSmol））	交互式图像;
	SMILES N([C@@H](Cc1ccccc1)C)C;
	InChI InChI=1S/C10H15N/c1-9(11-2)8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3/t9-/m1/s1 ; Key:MYWUZJCMWCOHBA-SECBINFHSA-N ;

左旋甲基苯丙胺 (levomethamphetamine)^{[note 1]}又称左旋甲基安非他命，是右旋甲基苯丙胺的光学异构体。左旋甲基苯丙胺是拟交感神经血管收缩剂，是一些非处方(OTC) 鼻腔去阻塞吸入剂（英语：nasal decongestant）的活性成分^{[note 2]}。

药理学特性

左旋甲基苯丙胺可穿越血脑屏障并作为TAAR1激动剂（英语：TAAR1 agonist）^[3]，也作为去甲肾上腺素释放剂（英语：norepinephrine releasing agent） (对多巴胺系统较无影响^[4])。它跟右旋甲基苯丙胺一样影响中枢神经系统，但作用方式不同^[5]。不同于右旋甲基苯丙胺，它在低剂量没有造成欣快或成瘾的特性^[5]^[6]^[4]。在他的几项生理作用中，血管收缩作用使其可用于去鼻腔阻塞喷剂^[7]。

左旋甲基苯丙胺的半衰期约为13.3至15小时，右旋甲基苯丙胺则为10.5小时^[8]。

参见

注释

^ 其他名字包含l-methamphetamine, levodesoxyephedrine, l-desoxyephedrine, levmetamfetamine (INN and USAN).
^ The active ingredient in some OTC inhalers in the United States is listed as levmetamfetamine, the INN and USAN of levomethamphetamine.^[1]^[2]

参考资料

^ CFR TITLE 21: DRUGS FOR HUMAN USE: PART 341 -- COLD, COUGH, ALLERGY, BRONCHODILATOR, AND ANTIASTHMATIC DRUG PRODUCTS FOR OVER-THE-COUNTER HUMAN USE. United States Food and Drug Administration. April 2015 [7 March 2016]. （原始内容存档于2019-12-25）. Topical nasal decongestants --(i) For products containing levmetamfetamine identified in 341.20(b)(1) when used in an inhalant dosage form. The product delivers in each 800 milliliters of air 0.04 to 0.150 milligrams of levmetamfetamine.
^ Levomethamphetamine. Pubchem Compound. National Center for Biotechnology Information. [2 January 2014]. （原始内容存档于2014-10-06）.
^ Levmetamfetamine. PubChem Compound. NCBI. [17 October 2014]. （原始内容存档于2014-10-18）.
^ ^4.0 ^4.1 Kuczenski, R; Segal, DS; Cho, AK; Melega, W. Hippocampus norepinephrine, caudate dopamine and serotonin, and behavioral responses to the stereoisomers of amphetamine and methamphetamine. The Journal of neuroscience : the official journal of the Society for Neuroscience. February 1995, 15 (2): 1308–17. PMID 7869099.
^ ^5.0 ^5.1 Melega, WP; Cho, AK; Schmitz, D; Kuczenski, R; Segal, DS. l-methamphetamine pharmacokinetics and pharmacodynamics for assessment of in vivo deprenyl-derived l-methamphetamine. The Journal of Pharmacology and Experimental Therapeutics. February 1999, 288 (2): 752–8. PMID 9918585.
^ Mendelson J, Uemura N, Harris D, Nath RP, Fernandez E, Jacob P, Everhart ET, Jones RT. Human pharmacology of the methamphetamine stereoisomers. Clinical pharmacology and therapeutics. October 2006, 80 (4): 403–20. PMID 17015058. doi:10.1016/j.clpt.2006.06.013.
^ {{cite web | author=Pray SW | title=Nonprescription Products to Avoid With Hypertension | work=uspharmacist.com | accessdate=17 October 2014 | url=http://www.uspharmacist.com/content/d/consult_your_pharmacist/c/19370/ （页面存档备份，存于互联网档案馆） | quote=Topical Nasal Decongestants
^ Mendelson J, Uemura N, Harris D, et al. Human pharmacology of the methamphetamine stereoisomers. Clin. Pharmacol. Ther. October 2006, 80 (4): 403–20. PMID 17015058. doi:10.1016/j.clpt.2006.06.013.

[1] 其他名字包含l-methamphetamine, levodesoxyephedrine, l-desoxyephedrine, levmetamfetamine (INN and USAN).

[OTC_levmetamfetamine-4] The active ingredient in some OTC inhalers in the United States is listed as levmetamfetamine, the INN and USAN of levomethamphetamine.^[1]^[2]

[FDA_levmetamfetamine-2] CFR TITLE 21: DRUGS FOR HUMAN USE: PART 341 -- COLD, COUGH, ALLERGY, BRONCHODILATOR, AND ANTIASTHMATIC DRUG PRODUCTS FOR OVER-THE-COUNTER HUMAN USE. United States Food and Drug Administration. April 2015 [7 March 2016]. （原始内容存档于2019-12-25）. Topical nasal decongestants --(i) For products containing levmetamfetamine identified in 341.20(b)(1) when used in an inhalant dosage form. The product delivers in each 800 milliliters of air 0.04 to 0.150 milligrams of levmetamfetamine.

[3] Levomethamphetamine. Pubchem Compound. National Center for Biotechnology Information. [2 January 2014]. （原始内容存档于2014-10-06）.

[TAAR1-5] Levmetamfetamine. PubChem Compound. NCBI. [17 October 2014]. （原始内容存档于2014-10-18）.

[PD-6] 4.0 ^4.1 Kuczenski, R; Segal, DS; Cho, AK; Melega, W. Hippocampus norepinephrine, caudate dopamine and serotonin, and behavioral responses to the stereoisomers of amphetamine and methamphetamine. The Journal of neuroscience : the official journal of the Society for Neuroscience. February 1995, 15 (2): 1308–17. PMID 7869099.

[Melega-7] 5.0 ^5.1 Melega, WP; Cho, AK; Schmitz, D; Kuczenski, R; Segal, DS. l-methamphetamine pharmacokinetics and pharmacodynamics for assessment of in vivo deprenyl-derived l-methamphetamine. The Journal of Pharmacology and Experimental Therapeutics. February 1999, 288 (2): 752–8. PMID 9918585.

[Mendelson2006-8] Mendelson J, Uemura N, Harris D, Nath RP, Fernandez E, Jacob P, Everhart ET, Jones RT. Human pharmacology of the methamphetamine stereoisomers. Clinical pharmacology and therapeutics. October 2006, 80 (4): 403–20. PMID 17015058. doi:10.1016/j.clpt.2006.06.013.

[9] {{cite web | author=Pray SW | title=Nonprescription Products to Avoid With Hypertension | work=uspharmacist.com | accessdate=17 October 2014 | url=http://www.uspharmacist.com/content/d/consult_your_pharmacist/c/19370/ （页面存档备份，存于互联网档案馆） | quote=Topical Nasal Decongestants

[pmid17015058-10] Mendelson J, Uemura N, Harris D, et al. Human pharmacology of the methamphetamine stereoisomers. Clin. Pharmacol. Ther. October 2006, 80 (4): 403–20. PMID 17015058. doi:10.1016/j.clpt.2006.06.013.

[note 1]

[note 2]

[3]

[4]

[5]

[6]

[7]

[8]

[1]

[2]