Benzphetamine (BioDeep_00000017955)

 

Secondary id: BioDeep_00000001905

human metabolite blood metabolite Chemicals and Drugs Volatile Flavor Compounds


代谢物信息卡片


(+)-N,alpha-Dimethyl-N-(phenylmethyl)-benzeneethanamine

化学式: C17H21N (239.1673906)
中文名称: N-苄基-N，α-二甲基苯乙胺, 苯丙胺
谱图信息: 最多检出来源 Homo sapiens(blood) 99.25%

分子结构信息

SMILES: CC(CC1=CC=CC=C1)N(C)CC2=CC=CC=C2
InChI: InChI=1S/C17H21N/c1-15(13-16-9-5-3-6-10-16)18(2)14-17-11-7-4-8-12-17/h3-12,15H,13-14H2,1-2H3

描述信息

Benzphetamine is only found in individuals that have used or taken this drug. It is a sympathomimetic agent with properties similar to dextroamphetamine. It is used in the treatment of obesity. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1222)Although the mechanism of action of the sympathomimetic appetite suppressants in the treatment of obesity is not fully known, these medications have pharmacological effects similar to those of amphetamines. Amphetamine and related sympathomimetic medications (such as benzphetamine) are thought to stimulate the release of norepinephrine and/or dopamine from storage sites in nerve terminals in the lateral hypothalamic feeding center, thereby producing a decrease in appetite. This release is mediated by the binding of benzphetamine to centrally located adrenergic receptors.
D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018759 - Adrenergic Uptake Inhibitors
D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018765 - Dopamine Uptake Inhibitors
D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D013566 - Sympathomimetics
D002491 - Central Nervous System Agents > D000697 - Central Nervous System Stimulants
C78272 - Agent Affecting Nervous System > C47795 - CNS Stimulant
D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents
C78272 - Agent Affecting Nervous System > C29728 - Anorexiant
D018377 - Neurotransmitter Agents > D015259 - Dopamine Agents
D049990 - Membrane Transport Modulators

同义名列表

32 个代谢物同义名

(+)-N,alpha-Dimethyl-N-(phenylmethyl)-benzeneethanamine; (+)-N,Α-dimethyl-N-(phenylmethyl)-benzeneethanamine; (+)-N,a-Dimethyl-N-(phenylmethyl)-benzeneethanamine; N-Methyl-1-phenyl-N-(phenylmethyl)propan-2-amine; (S)-(+)-N-Benzyl-N,alpha-dimethylphenethylamine; benzyl(methyl)[(2S)-1-phenylpropan-2-yl]amine; D-N-Methyl-N-benzyl-beta-phenylisopropylamine; (S)-(+)-N-Benzyl-N,α-dimethylphenethylamine; (+)-N-Benzyl-N,alpha-dimethylphenethylamine; (S)-(+)-N-Benzyl-N,a-dimethylphenethylamine; D-N-Methyl-N-benzyl-b-phenylisopropylamine; Pfizer brand OF benzfetamine hydrochloride; D-N-Methyl-N-benzyl-β-phenylisopropylamine; N-benzyl-N-methyl-1-phenylpropan-2-amine; (AlphaS)-N,alpha-dimethylphenethylamine; (+)-N-Benzyl-N,α-dimethylphenethylamine; (+)-N-Benzyl-N,a-dimethylphenethylamine; (AlphaS)-N,α-dimethylphenethylamine; (AlphaS)-N,a-dimethylphenethylamine; (S)-(+)-Benzphetamine; Benzylamphetamine; (+)-Benzphetamine; (S)-Benzphetamine; Benzaphetamine; Benzfetaminum; Benzphetamine; Benzfetamine; Benzfetamina; Didrex; Benzphetamine; Benzphetamine; N-Benzyl-N,alpha-dimethylphenethylamine



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

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PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Matthew L Banks, Rodney W Snyder, Timothy R Fennell, S Stevens Negus. Role of d-amphetamine and d-methamphetamine as active metabolites of benzphetamine: Evidence from drug discrimination and pharmacokinetic studies in male rhesus monkeys. Pharmacology, biochemistry, and behavior. 2017 05; 156(?):30-38. doi: 10.1016/j.pbb.2017.03.008. [PMID: 28373066]
  • Sandro Carrara, Andrea Cavallini, Victor Erokhin, Giovanni De Micheli. Multi-panel drugs detection in human serum for personalized therapy. Biosensors & bioelectronics. 2011 May; 26(9):3914-9. doi: 10.1016/j.bios.2011.03.009. [PMID: 21497079]
  • Sasan Mosadeghi, Bjarte Furnes, Aline Y O Matsuo, Daniel Schlenk. Expression and characterization of cytochrome P450 2X1 in channel catfish (Ictalurus punctatus). Biochimica et biophysica acta. 2007 Jul; 1770(7):1045-52. doi: 10.1016/j.bbagen.2007.03.008. [PMID: 17459590]
  • S G O'Brien, P Meinhardt, E Bond, J Beck, B Peng, C Dutreix, G Mehring, S Milosavljev, C Huber, R Capdeville, T Fischer. Effects of imatinib mesylate (STI571, Glivec) on the pharmacokinetics of simvastatin, a cytochrome p450 3A4 substrate, in patients with chronic myeloid leukaemia. British journal of cancer. 2003 Nov; 89(10):1855-9. doi: 10.1038/sj.bjc.6601152. [PMID: 14612892]
  • Sayeepriyadarshini Anakk, Chun Ying Ku, Mary Vore, Henry W Strobel. Insights into gender bias: rat cytochrome P450 3A9. The Journal of pharmacology and experimental therapeutics. 2003 May; 305(2):703-9. doi: 10.1124/jpet.102.048090. [PMID: 12606633]
  • Zoheir A Damanhouri. Mixed function oxidases in kidney and duodenum of camel, guinea pig and rat. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2002 Aug; 132(4):445-50. doi: 10.1016/s1532-0456(02)00099-6. [PMID: 12223200]
  • Yune-Fang Ueng, Ming-Jaw Don, Hsiao-Chi Peng, Shu-Yun Wang, Jong-Jing Wang, Chieh-Fu Chen. Effects of Wu-chu-yu-tang and its component herbs on drug-metabolizing enzymes. Japanese journal of pharmacology. 2002 Jul; 89(3):267-73. doi: 10.1254/jjp.89.267. [PMID: 12184732]
  • Emel Arinç, Haydar Celik, Haydar Lelik. Biochemical characteristics of purified beef liver NADPH-cytochrome P450 reductase. Journal of biochemical and molecular toxicology. 2002; 16(6):286-97. doi: 10.1002/jbt.10054. [PMID: 12481304]
  • Y F Ueng, J J Wang, L C Lin, S S Park, C F Chen. Induction of cytochrome P450-dependent monooxygenase in mouse liver and kidney by rutaecarpine, an alkaloid of the herbal drug Evodia rutaecarpa. Life sciences. 2001 Nov; 70(2):207-17. doi: 10.1016/s0024-3205(01)01390-x. [PMID: 11787945]
  • M Raynal, J D Bailly, G Benard, P Guerre. Effects of fumonisin B1 present in Fusarium moniliforme culture material on drug metabolising enzyme activities in ducks. Toxicology letters. 2001 May; 121(3):179-90. doi: 10.1016/s0378-4274(01)00338-1. [PMID: 11369472]
  • M Sato, T Mitsui, H Nagase. Analysis of benzphetamine and its metabolites in rat urine by liquid chromatography-electrospray ionization mass spectrometry. Journal of chromatography. B, Biomedical sciences and applications. 2001 Feb; 751(2):277-89. doi: 10.1016/s0378-4347(00)00482-5. [PMID: 11236083]
  • D Dai, R Bai, E Hodgson, R L Rose. Cloning, sequencing, heterologous expression, and characterization of murine cytochrome P450 3a25*(Cyp3a25), a testosterone 6beta-hydroxylase. Journal of biochemical and molecular toxicology. 2001; 15(2):90-9. doi: 10.1002/jbt.4. [PMID: 11284050]
  • C Calléja, K Bigot, C Eeckhoutte, P Sibille, C Boulard, P Galtier. Comparison of hepatic and renal drug-metabolising enzyme activities in sheep given single or two-fold challenge infections with Fasciola hepatica. International journal for parasitology. 2000 Jul; 30(8):953-8. doi: 10.1016/s0020-7519(00)00070-9. [PMID: 10927086]
  • F Musshoff. Illegal or legitimate use? Precursor compounds to amphetamine and methamphetamine. Drug metabolism reviews. 2000 Feb; 32(1):15-44. doi: 10.1081/dmr-100100562. [PMID: 10711406]
  • K L Baden, S Valtier, J T Cody. Metabolic production of amphetamine following multidose administration of clobenzorex. Journal of analytical toxicology. 1999 Oct; 23(6):511-7. doi: 10.1093/jat/23.6.511. [PMID: 10517559]
  • A Fujinami, T Miyazawa, N Tagawa, Y Kobayashi. Simultaneous analysis of benzphetamine and its metabolites, and quantitation of urinary p-hydroxy-N-benzylamphetamine by micellar electrokinetic chromatography. Biological & pharmaceutical bulletin. 1998 Nov; 21(11):1207-10. doi: 10.1248/bpb.21.1207. [PMID: 9853414]
  • A Fujinami, T Miyazawa, Y Kobayashi. Development of a method for the quantitation of benzphetamine metabolites in human urine by high-performance liquid chromatography. Annals of clinical biochemistry. 1998 Nov; 35 ( Pt 6)(?):775-9. doi: 10.1177/000456329803500611. [PMID: 9838992]
  • J T Cody, S Valtier. Detection of amphetamine and methamphetamine following administration of benzphetamine. Journal of analytical toxicology. 1998 Jul; 22(4):299-309. doi: 10.1093/jat/22.4.299. [PMID: 9681333]
  • P M Shaw, N A Hosea, D V Thompson, J M Lenius, F P Guengerich. Reconstitution premixes for assays using purified recombinant human cytochrome P450, NADPH-cytochrome P450 reductase, and cytochrome b5. Archives of biochemistry and biophysics. 1997 Dec; 348(1):107-15. doi: 10.1006/abbi.1997.0378. [PMID: 9390180]
  • R Kikura, Y Nakahara. Hair analysis for drugs of abuse. XI. Disposition of benzphetamine and its metabolites into hair and comparison of benzphetamine use and methamphetamine use by hair analysis. Biological & pharmaceutical bulletin. 1995 Dec; 18(12):1694-9. doi: 10.1248/bpb.18.1694. [PMID: 8787790]
  • K A Moore, A Poklis. alpha-Benzyl-N-methylphenethylamine (BNMPA), an impurity of illicit methamphetamine synthesis: II. Metabolism and urinary excretion (human). Journal of analytical toxicology. 1995 Nov; 19(7):549-53. doi: 10.1093/jat/19.7.549. [PMID: 8577176]
  • S S Ahmed, K L Napoli, H W Strobel. Oxygen radical formation during cytochrome P450-catalyzed cyclosporine metabolism in rat and human liver microsomes at varying hydrogen ion concentrations. Molecular and cellular biochemistry. 1995 Oct; 151(2):131-40. doi: 10.1007/bf01322335. [PMID: 8569758]
  • M J Choi, J Choi, J Park, S A Eremin. Localization of the epitope in methamphetamine and its antibody use for the detection of methamphetamine and benzphetamine by polarization fluoroimmunoassay. Journal of immunoassay. 1995 Aug; 16(3):263-78. doi: 10.1080/15321819508013562. [PMID: 7593649]
  • J B Watkins, J W LaFollette, R A Sanders. Biotransformation in Egyptian spiny mouse Acomys cahirinus. Comparative biochemistry and physiology. Part C, Pharmacology, toxicology & endocrinology. 1995 Jan; 110(1):101-7. doi: 10.1016/0742-8413(94)00104-i. [PMID: 7749597]
  • E Arinç, R P Pasha, O Adali, N Başaran. Stimulatory effects of lung cytochrome b5 on benzphetamine N-demethylation in a reconstituted system containing lung cytochrome P450LgM2. The International journal of biochemistry. 1994 Aug; 26(8):1033-42. doi: 10.1016/0020-711x(94)90075-2. [PMID: 8088413]
  • D E Ryan, P E Thomas, W Levin, S L Maines, S Bandiera, L M Reik. Monoclonal antibodies of differentiating specificities as probes of cytochrome P450h (2C11). Archives of biochemistry and biophysics. 1993 Mar; 301(2):282-93. doi: 10.1006/abbi.1993.1145. [PMID: 7681658]
  • H Yamada, H Kaneko, K Takeuchi, K Oguri, H Yoshimura. Tissue-specific expression, induction, and inhibition through metabolic intermediate-complex formation of guinea pig cytochrome P450 belonging to the CYP2B subfamily. Archives of biochemistry and biophysics. 1992 Dec; 299(2):248-54. doi: 10.1016/0003-9861(92)90271-w. [PMID: 1444463]
  • Z A al-Bayati, S J Stohs. The possible role of phospholipase A2 in hepatic microsomal lipid peroxidation induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin in rats. Archives of environmental contamination and toxicology. 1991 Apr; 20(3):361-5. doi: 10.1007/bf01064403. [PMID: 1859207]
  • A Franceschini, J M Duthel, J J Vallon. [Specific detection of urinary sympathomimetic amines for control of anti-doping by gas chromatography-mass spectroscopy]. Journal of chromatography. 1991 Mar; 541(1-2):109-20. doi: 10.1016/s0021-9673(01)95988-6. [PMID: 2037649]
  • T Inoue, S Suzuki. The metabolism of 1-phenyl-2-(N-methyl-N-benzylamino)propane (benzphetamine) and 1-phenyl-2-(N-methyl-N-furfurylamino)propane (furfenorex) in man. Xenobiotica; the fate of foreign compounds in biological systems. 1986 Jul; 16(7):691-8. doi: 10.3109/00498258609043559. [PMID: 3751123]
  • H Taniguchi, Y Imai, R Sato. Substrate binding site of microsomal cytochrome P-450 directly faces membrane lipids. Biochemical and biophysical research communications. 1984 Feb; 118(3):916-22. doi: 10.1016/0006-291x(84)91482-7. [PMID: 6704114]
  • A A Ademoyero, R R Dalvi. Efficacy of activated charcoal and other agents in the reduction of hepatotoxic effects of a single dose of aflatoxin B1 in chickens. Toxicology letters. 1983 Apr; 16(1-2):153-7. doi: 10.1016/0378-4274(83)90024-3. [PMID: 6404013]
  • S D Mercurio, A M Nemeth. Regulation of monooxygenation during development of chick embryo liver: role of cytochrome P-450 isozymes and NADPH. Developmental pharmacology and therapeutics. 1983; 6(2):94-109. doi: 10.1159/000457283. [PMID: 6861599]
  • R Greinert, S A Finch, A Stier. Cytochrome P-450 rotamers control mixed-function oxygenation in reconstituted membranes. Rotational diffusion studied by delayed fluorescence depolarization. Xenobiotica; the fate of foreign compounds in biological systems. 1982 Nov; 12(11):717-26. doi: 10.3109/00498258209038946. [PMID: 7168192]
  • T Niwaguchi, T Inoue, S Suzuki. The metabolism of 1-phenyl-2-(N-methyl-N-benzylamino)propane (benzphetamine) in vivo in the rat. Xenobiotica; the fate of foreign compounds in biological systems. 1982 Oct; 12(10):617-25. doi: 10.3109/00498258209042040. [PMID: 7157832]
  • C D Blitt, A J Gandolfi, J J Soltis, B R Brown. Extrahepatic biotransformation of halothane and enflurane. Anesthesia and analgesia. 1981 Mar; 60(3):129-32. doi: NULL. [PMID: 7193988]
  • M Vore, E Soliven. Organic solvent extraction of liver microsomal lipid. Effect on the kinetic parameters of benzo[a]pyrene hydroxylase and benzphetamine N-demethylase activity. Biochemical pharmacology. 1979 Dec; 28(24):3659-65. doi: 10.1016/0006-2952(79)90413-1. [PMID: 533563]
  • M Warner, A H Neims. Multiple forms of ethoxyresorufin O-de-ethylase and benzphetamine N-demethylase in solubilized and partially resolved rat liver cytochromes P-450. Drug metabolism and disposition: the biological fate of chemicals. 1979 May; 7(3):188-93. doi: . [PMID: 38092]
  • L S Nerurkar, J R Hayes, T C Campbell. The reconstitution of hepatic microsomal mixed function oxidase activity with fractions derived from weanling rats fed different levels of protein. The Journal of nutrition. 1978 Apr; 108(4):678-86. doi: 10.1093/jn/108.4.678. [PMID: 416184]
  • M Black, L Biempica, S Goldfischer, S Grossman, I M Arias. Effect of chronic renal failure in rats on structure and function of the hepatic endoplasmic reticulum. Experimental and molecular pathology. 1977 Dec; 27(3):377-91. doi: 10.1016/0014-4800(77)90008-9. [PMID: 923751]
  • J G Joly, C Hétu. Effects of chronic ethanol administration in the rat: relative dependency on dietary lipids. II. Paradoxical role of linoleate in the induction of hepatic drug-metabolizing enzymes in vitro. Canadian journal of physiology and pharmacology. 1977 Feb; 55(1):34-41. doi: 10.1139/y77-005. [PMID: 402995]
  • R R Dalvi, C D Howell. Toxic effects of a fungicide, 5-ethoxy-3-(trichloromethy)-1,2,4-thiadiazole (terrazole), on the hepatic drug metabolizing enzyme system in mice. Bulletin of environmental contamination and toxicology. 1977 Feb; 17(2):225-32. doi: 10.1007/bf01685555. [PMID: 843640]
  • H A Sasame, S S Thorgeirsson, J R Mitchell, J R Gillette. The role of cytochrome b5 in cytochrome P-450 enzymes. Advances in experimental medicine and biology. 1975; 58(00):435-45. doi: 10.1007/978-1-4615-9026-2_30. [PMID: 239544]
  • A Y Lu, W Levin, S B West, M Vore, D Ryan, R Kuntzman, A H Conney. Role of cytochrome b5 in NADPH-and NADH-dependent hydroxylation by the reconstituted cytochrome P-450- or P-448-containing system. Advances in experimental medicine and biology. 1975; 58(00):447-66. doi: 10.1007/978-1-4615-9026-2_31. [PMID: 239545]
  • W Levin, A Y Lu, D Ryan, S k West, R Kuntzman, A H Conney. Partial purification and separation of multiple forms of cytochrome. P-450 and cytochrome P-448 from rat liver microsomes. Advances in experimental medicine and biology. 1975; 58(00):1-24. doi: 10.1007/978-1-4615-9026-2_1. [PMID: 808108]
  • A Y Lu, W Levin, R Kuntzman. Reconstituted liver microsomal enzyme system that hydroxylates drugs, other foreign compounds and endogenous substrates. VII. Stimulation of benzphetamine N-demethylation by lipid and detergent. Biochemical and biophysical research communications. 1974 Sep; 60(1):266-72. doi: 10.1016/0006-291x(74)90200-9. [PMID: 4371318]
  • W Levin, A Y Lu, M Jacobson, R Kuntzman, J L Poyer, P B McCay. Lipid peroxidation and the degradation of cytochrome P-450 heme. Archives of biochemistry and biophysics. 1973 Oct; 158(2):842-52. doi: 10.1016/0003-9861(73)90580-8. [PMID: 4150126]
  • A Y Lu, H W Strobel, M J Coon. Properties of a solubilized form of the cytochrome P-450-containing mixed-function oxidase of liver microsomes. Molecular pharmacology. 1970 May; 6(3):213-20. doi: ". [PMID: 4315336]
  • T B Vree, A T Muskens, J M van Rossum. Some physico-chemical properties of amphetamine and related drugs. The Journal of pharmacy and pharmacology. 1969 Nov; 21(11):774-5. doi: 10.1111/j.2042-7158.1969.tb08168.x. [PMID: 4390837]
  • A Y Lu, H W Strobel, M J Coon. Hydroxylation of benzphetamine and other drugs by a solubilized form of cytochrome P-450 from liver microsomes: lipid requirement for drug demethylation. Biochemical and biophysical research communications. 1969 Aug; 36(4):545-51. doi: 10.1016/0006-291x(69)90339-8. [PMID: 4390187]
  • A H Beckett, E J Triggs. Buccal absorption of basic drugs and its application as an in vivo model of passive drug transfer through lipid membranes. The Journal of pharmacy and pharmacology. 1967 Dec; 19(?):Suppl:31S-41S. doi: ". [PMID: 4383854]