左旋甲基苯丙胺

左旋甲基苯丙胺
臨床資料
給藥途徑	醫用 :吸入(鼻腔); 娛樂用 :口服靜脈注射, insufflation,吸入栓劑
法律規範狀態
法律規範	加：Schedule I; 德：Anlage II; 英：Class A; 美：Schedule II（英語：Controlled Substances Act#Schedule II drugs）;特定配方為OTC; UN：Psychotropic Schedule II;
藥物動力學數據
藥物代謝	肝臟
排泄途徑	腎
識別資訊
	IUPAC命名法 (R)-N-methyl-1-phenyl-propan-2-amine; ;
CAS號	33817-09-3
PubChem CID	36604;
ChemSpider	33634 ;
UNII	44RAL3456C;
KEGG	D02291 ;
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID30187474 ;
ECHA InfoCard	100.046.974
化學資訊
化學式	C10H15N
摩爾質量	149.2
3D模型（JSmol（英語：JSmol））	交互式圖像;
	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]}又稱左旋甲基安非他命，是右旋甲基苯丙胺的旋光異構體。左旋甲基苯丙胺是擬交感神經血管收縮劑，是一些非處方(OTC) 鼻腔去阻塞吸入劑（英語：nasal decongestant）的活性成分^{[note 2]}。

藥理學特性

左旋甲基苯丙胺可穿越血腦屏障並作為TAAR1激動劑（英語：TAAR1 agonist）^[3]，也作為去甲腎上腺素釋放劑（英語：norepinephrine releasing agent） (對多巴胺系統較無影響^[4])。它跟右旋甲基苯丙胺一樣影響中樞神經系統，但作用方式不同^[5]。不同於右旋甲基苯丙胺，它在低劑量沒有造成欣快或成癮的特性^[5]^[6]^[4]。在他的幾項生理作用中，血管收縮作用使其可用於去鼻腔阻塞噴劑^[7]。

左旋甲基苯丙胺的半衰期約為13.3至15小時，右旋甲基苯丙胺則為10.5小時^[8]。

參見

注釋

^ 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]

參考資料

^ 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]. （原始內容存檔於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]. （原始內容存檔於2014-10-06）.
^ Levmetamfetamine. PubChem Compound. NCBI. [17 October 2014]. （原始內容存檔於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/ （頁面存檔備份，存於網際網路檔案館） | 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]. （原始內容存檔於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]. （原始內容存檔於2014-10-06）.

[TAAR1-5] Levmetamfetamine. PubChem Compound. NCBI. [17 October 2014]. （原始內容存檔於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/ （頁面存檔備份，存於網際網路檔案館） | 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.

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