右旋安非他命

右旋安非他命
INN： Dexamfetamine
臨床資料
AHFS/Drugs.com	Monograph
MedlinePlus	a605027
核准狀況	美 FDA: Dextroamphetamine;
懷孕分級	澳: B3 ; ;
依賴性	生理依賴：無; 精神依賴：中
成癮性	中
給藥途徑	口服
ATC碼	N06BA02 (WHO) ;
法律規範狀態
法律規範	澳：受管控（S8）; 加：Schedule I; 德：Anlage III; 英：Class B; 美：附表II;
藥物動力學數據
生物利用度	Oral 75–100%
血漿蛋白結合率	15–40%
藥物代謝	CYP2D6，多巴胺β羥化酶， FMO3（英語：Flavin-containing monooxygenase）
藥效起始時間（英語：Onset of action）	IR服用：0.5至1.5小時; XR服用：1.5至2小時
生物半衰期	9至11小時; 不同的PH值：8至31小時
作用時間	IR服用：3至7小時; XR服用：12小時
排泄途徑	腎（45%）；取決於尿液的pH值
識別資訊
	IUPAC命名法 (2S)-1-phenylpropan-2-amine; ;
CAS編號	51-64-9
PubChem CID	5826;
IUPHAR/BPS	2147;
DrugBank	DB01576 ;
ChemSpider	5621 ;
UNII	TZ47U051FI;
KEGG	D03740 ;
ChEBI	CHEBI:4469 ;
ChEMBL	ChEMBL612 ;
CompTox Dashboard（英語：CompTox Chemicals Dashboard） (EPA)	DTXSID8022907 ;
ECHA InfoCard	100.000.103
化學資訊
化學式	C9H13N
摩爾質量	135.20622
3D模型（JSmol（英語：JSmol））	交互式圖像;
密度	0.913 g/cm3
沸點	201.5 °C（394.7 °F）
水溶性	20 mg/mL (20 °C)
	SMILES C[C@@H](Cc1ccccc1)N;
	InChI InChI=InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m0/s1 ; Key:KWTSXDURSIMDCE-QMMMGPOBSA-N ;

右旋安非他命（INN：dexamfetamine，USAN：dextroamphetamine）^{[注 1]}是強力中樞神經興奮劑，也是苯丙胺（「安非他命」）的對映異構體，是注意力不足過動症（ADHD）和發作性嗜睡病的處方藥^[10]。常見商品名為 Dexedrine^[11]^[12]。

此外也存在一些濫用，如：被用作提升運動員能力的興奮劑，或作一種益智藥，同時人們在享樂時也將其用作春藥和產生欣快感的藥。以往，空軍也將右旋安非他命廣泛用作「抗睡丸」，在諸如夜間轟炸之類的容易疲倦的任務中使用。第二次世界大戰期間，該藥物也被用來治療疲倦。

腳註

^ 其他英文名稱：dexamphetamine （AAN（英語：Australian Approved Name））、dexamfetamine （BAN（英語：British Approved Name））、(S)-amphetamine、(+)-amphetamine、D-amphetamine。

參考資料

^ Dextromphetamine. DrugBank. [2013-11-05]. （原始內容存檔於2019-08-06）. |section=被忽略 (幫助)
^ Green-Hernandez, Carol; Singleton, Joanne K.; Aronzon, Daniel Z. Primary Care Pediatrics. Lippincott Williams & Wilkins. 2001-01-01: 243 [2017-05-07]. ISBN 9780781720083. （原始內容存檔於2016-05-23）. |quote = Table 21.2 Medications for ADHD ... D-amphetamine ... Onset: 30 min.
^ Dexedrine, ProCentra(dextroamphetamine) dosing, indications, interactions, adverse effects, and more. reference.medscape.com. [2015-10-04]. （原始內容存檔於2018-11-06）. Onset of action: 1–1.5 hr
^ ^4.0 ^4.1 ^4.2 Millichap JG. Chapter 9: Medications for ADHD. Millichap JG (編). Attention Deficit Hyperactivity Disorder Handbook: A Physician's Guide to ADHD 2nd. New York, USA: Springer. 2010: 112. ISBN 9781441913968.
Table 9.2 Dextroamphetamine formulations of stimulant medication
Dexedrine [Peak:2–3 h] [Duration:5–6 h] ...
Adderall [Peak:2–3 h] [Duration:5–7 h]
Dexedrine spansules [Peak:7–8 h] [Duration:12 h] ...
Adderall XR [Peak:7–8 h] [Duration:12 h]
Vyvanse [Peak:3–4 h] [Duration:12 h]
^ ^5.0 ^5.1 Brams M, Mao AR, Doyle RL. Onset of efficacy of long-acting psychostimulants in pediatric attention-deficit/hyperactivity disorder. Postgrad. Med. September 2008, 120 (3): 69–88. PMID 18824827. doi:10.3810/pgm.2008.09.1909. Onset of efficacy was earliest for d-MPH-ER at 0.5 hours, followed by d, l-MPH-LA at 1 to 2 hours, MCD at 1.5 hours, d, l-MPH-OR at 1 to 2 hours, MAS-XR at 1.5 to 2 hours, MTS at 2 hours, and LDX at approximately 2 hours. ... MAS-XR, and LDX have a long duration of action at 12 hours postdose
^ Adderall IR Prescribing Information (PDF). United States Food and Drug Administration. Teva Pharmaceuticals USA, Inc.: 1–6. October 2015 [2016-05-18]. （原始內容存檔 (PDF)於2018-09-15）.
^ ^7.0 ^7.1 Mignot EJ. A practical guide to the therapy of narcolepsy and hypersomnia syndromes. Neurotherapeutics. October 2012, 9 (4): 739–752. PMC 3480574  . PMID 23065655. doi:10.1007/s13311-012-0150-9.
^ dextrostat (dextroamphetamine sulfate) tablet [Shire US Inc.]. DailyMed. Wayne, PA: Shire US Inc. August 2006 [2013-11-08]. （原始內容存檔於2012-01-13）.
^ Lemke TL, Williams DA, Roche VF, Zito W. Foye's Principles of Medicinal Chemistry 7th. Philadelphia: Wolters Kluwer Health/Lippincott Williams & Wilkins. 2013: 648. ISBN 1609133455. Alternatively, direct oxidation of amphetamine by DA β-hydroxylase can afford norephedrine.
^ Dexedrine Prescribing Information (PDF). United States Food and Drug Administration. Amedra Pharmaceuticals LLC: 1–7. February 2015 [2015-09-04]. （原始內容存檔 (PDF)於2017-02-17）.
^ Dexedrine spansule- dextroamphetamine sulfate capsule, extended release. DailyMed. 10 January 2022 [28 March 2022].
^ Dexedrine. Medic8. [27 November 2013]. （原始內容存檔於19 December 2009）.

[10] 其他英文名稱：dexamphetamine （AAN（英語：Australian Approved Name））、dexamfetamine （BAN（英語：British Approved Name））、(S)-amphetamine、(+)-amphetamine、D-amphetamine。

[1] Dextromphetamine. DrugBank. [2013-11-05]. （原始內容存檔於2019-08-06）. |section=被忽略 (幫助)

[2] Green-Hernandez, Carol; Singleton, Joanne K.; Aronzon, Daniel Z. Primary Care Pediatrics. Lippincott Williams & Wilkins. 2001-01-01: 243 [2017-05-07]. ISBN 9780781720083. （原始內容存檔於2016-05-23）. |quote = Table 21.2 Medications for ADHD ... D-amphetamine ... Onset: 30 min.

[3] Dexedrine, ProCentra(dextroamphetamine) dosing, indications, interactions, adverse effects, and more. reference.medscape.com. [2015-10-04]. （原始內容存檔於2018-11-06）. Onset of action: 1–1.5 hr

[Millichap:_onset,_peak,_and_duration-4] 4.0 ^4.1 ^4.2 Millichap JG. Chapter 9: Medications for ADHD. Millichap JG (編). Attention Deficit Hyperactivity Disorder Handbook: A Physician's Guide to ADHD 2nd. New York, USA: Springer. 2010: 112. ISBN 9781441913968.
Table 9.2 Dextroamphetamine formulations of stimulant medication
Dexedrine [Peak:2–3 h] [Duration:5–6 h] ...
Adderall [Peak:2–3 h] [Duration:5–7 h]
Dexedrine spansules [Peak:7–8 h] [Duration:12 h] ...
Adderall XR [Peak:7–8 h] [Duration:12 h]
Vyvanse [Peak:3–4 h] [Duration:12 h]

[XR_onset-duration-5] 5.0 ^5.1 Brams M, Mao AR, Doyle RL. Onset of efficacy of long-acting psychostimulants in pediatric attention-deficit/hyperactivity disorder. Postgrad. Med. September 2008, 120 (3): 69–88. PMID 18824827. doi:10.3810/pgm.2008.09.1909. Onset of efficacy was earliest for d-MPH-ER at 0.5 hours, followed by d, l-MPH-LA at 1 to 2 hours, MCD at 1.5 hours, d, l-MPH-OR at 1 to 2 hours, MAS-XR at 1.5 to 2 hours, MTS at 2 hours, and LDX at approximately 2 hours. ... MAS-XR, and LDX have a long duration of action at 12 hours postdose

[Adderall_IR-6] Adderall IR Prescribing Information (PDF). United States Food and Drug Administration. Teva Pharmaceuticals USA, Inc.: 1–6. October 2015 [2016-05-18]. （原始內容存檔 (PDF)於2018-09-15）.

[Narcolepsy_guide-7] 7.0 ^7.1 Mignot EJ. A practical guide to the therapy of narcolepsy and hypersomnia syndromes. Neurotherapeutics. October 2012, 9 (4): 739–752. PMC 3480574  . PMID 23065655. doi:10.1007/s13311-012-0150-9.

[8] xtrostat (dextroamphetamine sulfate) tablet [Shire US Inc.]. DailyMed. Wayne, PA: Shire US Inc. August 2006 [2013-11-08]. （原始內容存檔於2012-01-13）.

[DBH_ref-9] Lemke TL, Williams DA, Roche VF, Zito W. Foye's Principles of Medicinal Chemistry 7th. Philadelphia: Wolters Kluwer Health/Lippincott Williams & Wilkins. 2013: 648. ISBN 1609133455. Alternatively, direct oxidation of amphetamine by DA β-hydroxylase can afford norephedrine.

[Dexedrine-11] Dexedrine Prescribing Information (PDF). United States Food and Drug Administration. Amedra Pharmaceuticals LLC: 1–7. February 2015 [2015-09-04]. （原始內容存檔 (PDF)於2017-02-17）.

[Dexedrine_FDA_label-12] Dexedrine spansule- dextroamphetamine sulfate capsule, extended release. DailyMed. 10 January 2022 [28 March 2022].

[13] Dexedrine. Medic8. [27 November 2013]. （原始內容存檔於19 December 2009）.

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