EXPERIENCESWITH DMT (Dimethyltryptamine) I'i TIMQTHY/EARY
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Comparison of the Characteristic Mass Fragmentations of Phenethylamines and Tryptamines by Electron Ionization Gas Chromatograph
applied sciences Article Comparison of the Characteristic Mass Fragmentations of Phenethylamines and Tryptamines by Electron Ionization Gas Chromatography Mass Spectrometry, Electrospray and Matrix-Assisted Laser Desorption Ionization Mass Spectrometry Bo-Hong Chen, Ju-Tsung Liu, Hung-Ming Chen, Wen-Xiong Chen and Cheng-Huang Lin * Department of Chemistry, National Taiwan Normal University, 88 Sec. 4 Tingchow Road, Taipei 11677, Taiwan; [email protected] (B.-H.C.); [email protected] (J.-T.L.); [email protected] (H.-M.C.); [email protected] (W.-X.C.) * Correspondence: [email protected]; Tel.: +886-2-7734-6170; Fax: +886-2-2932-4249 Received: 18 April 2018; Accepted: 19 June 2018; Published: 22 June 2018 Abstract: Characteristic mass fragmentation of 20 phenethylamine/tryptamine standards were investigated and compared by means of matrix assisted laser desorption/time-of-flight mass spectrometry (MALDI/TOFM), gas chromatography–electron ionization–mass spectrometry (GC-EI/MS) and liquid chromatography–electrospray ionization/mass spectrometry (LC-ESI/MS) + methods. As a result, three characteristic peaks ([M] and fragments from the Cβ-Cα bond breakage) were found to be unique and contained information useful in identifying 2C series compounds based on the GC-EI/MS method. We found that the protonated molecular ion ([M+H]+) and two types of fragments produced from the α-cleavage and β-cleavage processes were useful mass spectral information in the rapid screening and confirmation of phenethylamine and tryptamine derivatives when ESI/MS and MALDI/TOFMS methods were applied. This assay was successfully used to determine samples that contain illicit drugs. Keywords: phenethylamine; tryptamine; MALDI/TOFMS; GC-EI/MS; LC-ESI/MS 1. -
Virginia Acts of Assembly -- 2021 Special Session I
VIRGINIA ACTS OF ASSEMBLY -- 2021 SPECIAL SESSION I CHAPTER 110 An Act to amend and reenact §§ 3.2-4112, 3.2-4113, 3.2-4114.2, 3.2-4115, 3.2-4116, 3.2-4118, 3.2-4119, 18.2-247, 18.2-251.1:3, 54.1-3401, and 54.1-3446 of the Code of Virginia, relating to industrial hemp; emergency. [H 2078] Approved March 12, 2021 Be it enacted by the General Assembly of Virginia: 1. That §§ 3.2-4112, 3.2-4113, 3.2-4114.2, 3.2-4115, 3.2-4116, 3.2-4118, 3.2-4119, 18.2-247, 18.2-251.1:3, 54.1-3401, and 54.1-3446 of the Code of Virginia are amended and reenacted as follows: § 3.2-4112. Definitions. As used in this chapter, unless the context requires a different meaning: "Cannabis sativa product" means a product made from any part of the plant Cannabis sativa, including seeds thereof and any derivative, extract, cannabinoid, isomer, acid, salt, or salt of an isomer, whether growing or not, with a concentration of tetrahydrocannabinol that is greater than that allowed by federal law. "Deal" means to buy temporarily possess industrial hemp grown in compliance with state or federal law and to sell such industrial hemp to a person who that (i) processes industrial hemp in compliance with state or federal law or has not been processed and (ii) sells industrial hemp to a person who processes industrial hemp in compliance with state or federal law was not grown and will not be processed by the person temporarily possessing it. -
A General Approach to the Screening and Confirmation of Tryptamines And
Available online at www.sciencedirect.com Talanta 74 (2008) 512–517 A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation Bo-Hong Chen a, Ju-Tsung Liu b, Wen-Xiong Chen a, Hung-Ming Chen a, Cheng-Huang Lin a,∗ a Department of Chemistry, National Taiwan Normal University, 88 Sec. 4, Tingchow Road, Taipei, Taiwan b Forensic Science Center, Military Police Command, Department of Defense, Taipei, Taiwan Received 6 March 2007; received in revised form 12 June 2007; accepted 13 June 2007 Available online 19 June 2007 Abstract Certain characteristic fragmentations of tryptamines (indoleethylamine) and phenethylamines are described. Based on the GC–EI/MS, LC–ESI/ MS and MALDI/TOFMS, the mass fragmentations of 13 standard compounds, including ␣-methyltryptamine (AMT), N,N-dimethyltryptamine (DMT), 5-methoxy-␣-methyltryptamine (5-MeO-AMT), N,N-diethyltryptamine (DET), N,N-dipropyltryptamine (DPT), N,N-dibutyltryptamine (DBT), N,N-diisopropyltryptamine (DIPT), 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT), 5-methoxy-N,N-diisopropyltryptamine (5-MeO- DIPT), methamphetamine (MAMP), 3,4-methylenedioxyamphetamine (3,4-MDA), 3,4-methylenedioxymethamphetamine (3,4-MDMA) and 2- methylamino-1-(3,4-methylenedioxyphenyl)butane (MBDB), were compared. As a result, the parent ions of these analytes were hard to be obtained by GC/MS whereas the protonated molecular ions can be observed clearly by means of ESI/MS and MALDI/TOFMS. Furthermore, two major + + + + characteristic fragmentations, namely and ␣-cleavage ([M +H] → [3-vinylindole] ) and -cleavage ([M +H] → [CH2N RN1RN2]), are produced when the ESI and MALDI modes are used, respectively. In the case of ESI/MS, the fragment obtained from ␣-cleavage is the major process. -
Application of High Resolution Mass Spectrometry for the Screening and Confirmation of Novel Psychoactive Substances Joshua Zolton Seither [email protected]
Florida International University FIU Digital Commons FIU Electronic Theses and Dissertations University Graduate School 4-25-2018 Application of High Resolution Mass Spectrometry for the Screening and Confirmation of Novel Psychoactive Substances Joshua Zolton Seither [email protected] DOI: 10.25148/etd.FIDC006565 Follow this and additional works at: https://digitalcommons.fiu.edu/etd Part of the Chemistry Commons Recommended Citation Seither, Joshua Zolton, "Application of High Resolution Mass Spectrometry for the Screening and Confirmation of Novel Psychoactive Substances" (2018). FIU Electronic Theses and Dissertations. 3823. https://digitalcommons.fiu.edu/etd/3823 This work is brought to you for free and open access by the University Graduate School at FIU Digital Commons. It has been accepted for inclusion in FIU Electronic Theses and Dissertations by an authorized administrator of FIU Digital Commons. For more information, please contact [email protected]. FLORIDA INTERNATIONAL UNIVERSITY Miami, Florida APPLICATION OF HIGH RESOLUTION MASS SPECTROMETRY FOR THE SCREENING AND CONFIRMATION OF NOVEL PSYCHOACTIVE SUBSTANCES A dissertation submitted in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY in CHEMISTRY by Joshua Zolton Seither 2018 To: Dean Michael R. Heithaus College of Arts, Sciences and Education This dissertation, written by Joshua Zolton Seither, and entitled Application of High- Resolution Mass Spectrometry for the Screening and Confirmation of Novel Psychoactive Substances, having been approved in respect to style and intellectual content, is referred to you for judgment. We have read this dissertation and recommend that it be approved. _______________________________________ Piero Gardinali _______________________________________ Bruce McCord _______________________________________ DeEtta Mills _______________________________________ Stanislaw Wnuk _______________________________________ Anthony DeCaprio, Major Professor Date of Defense: April 25, 2018 The dissertation of Joshua Zolton Seither is approved. -
NFLIS-Drug Selected Substance List
2017-2020 NFLIS-Drug Substance List (Sorted by Date) Date Added NFLIS Substance Name Synonyms Chemical Name Structure InChI Formula to NFLIS- Drug InChI=1S/C16H20BrN/ c17-14-1-3-15(4-2-14)18-16-12-6-10-5-11 Bromantane ladasten N-(4-bromophenyl)adamantan-2-amine C16H20BrN 12/7/20 (8-12)9-13(16)7-10/h1-4,10-13,16,18H, 5-9H2 InChI=1S/C21H29FN2O3/ c1-4-27-21(26)19(15(2)3)23-20(25)17-14- ethyl 2-(1-(5-fluoropentyl)-1H-indole-3-carboxamido)-3- 5F-EMB-PICA EMB-2201; 5-fluoro-EMB-PICA 24(13-9-5-8-12-22)18-11-7-6-10-16(17)18 C21H29FN2O3 11/12/20 methylbutanoate /h6-7,10-11,14-15,19H, 4-5,8-9,12-13H2,1-3H3,(H,23,25) InChI=1S/C20H27FN2O3/ c1-20(2,3)17(19(25)26-4)22-18(24)15-13- methyl 2-(1-(4-fluorobutyl)-1H-indole-3- 4F-MDMB-BUTICA 4-fluoro-MDMB-BUTICA; 4F-MDMB-BICA 23(12-8-7-11-21)16-10-6-5-9-14(15)16/ C20H27FN2O3 10/23/20 carboxamido)-3,3-dimethylbutanoate h5-6,9-10,13,17H,7-8,11-12H2,1-4H3,(H, 22,24) InChI=1S/C10H14BrNO2/ 4-methoxy-6-[(1E)-2-phenylethenyl]-5,6-dihydro-2H- 2Br-4,5-Dimethoxyphenethylamine 2-bromo-4,5-dimethoxyphenethylamine c1-13-9-5-7(3-4-12)8(11)6-10(9)14-2/ C10H14BrNO2 10/2/20 pyran-2-one h5-6H,3-4,12H2,1-2H3 InChI=1S/C16H22FNO/ 4-fluoro-3-methyl-alpha-PVP; 4F-3-methyl-alpha- c1-3-6-15(18-9-4-5-10-18)16(19)13-7-8-1 4F-3-Methyl-alpha-PVP 4-fluoro-3-methyl-alpha-pyrrolidinopentiophenone C16H22FNO 10/2/20 pyrrolidinovalerophenone 4(17)12(2)11-13/h7-8,11,15H, 3-6,9-10H2,1-2H3 InChI=1S/C21H26N4O3/ N,N-diethyl-2-[2-(4-methoxybenzyl)-5-nitro-1H- c1-4-23(5-2)12-13-24-20-11-8-17(25(26)2 Metonitazene C21H26N4O3 9/15/20 benzimidazol-1-yl]ethanamine -
Computational Chemoproteomics to Understand the Role of Selected Psychoactives in Treating Mental Health Indications
Computational chemoproteomics to understand the role of selected psychoactives in treating mental health indications Jonathan Fine∗ Rachel Lackner† Ram Samudrala§¶ Gaurav Chopra∗‡¶ ∗ Department of Chemistry, Purdue University, West Lafayette, IN, USA † Yale University, New Haven, CT, USA ‡ Purdue Institute for Drug Discovery, Purdue Institute for Integrative Neuroscience, Purdue Institute for Integrative Neuroscience, Purdue Institute for Immunology, Inflammation and Infectious Disease, Purdue Center for Cancer Research, West Lafayette, IN, USA § Department of Biomedical Informatics, SUNY, Buffalo, NY, USA ¶ Corresponding authors: [email protected], [email protected] Abstract We have developed the Computational Analysis of Novel Drug Opportunities (CANDO) platform to infer homology of drug behavior at a proteomic level by constructing and analyzing structural compound-proteome interaction signatures of 3,733 compounds with 48,278 proteins in a shotgun manner. We applied the CANDO platform to predict putative therapeutic properties of 428 psychoactive compounds that belong to phenylethylamine, tryptamine, and cannabinoid chemical classes for treating mental health indications. Our findings indicate that these 428 psychoactives are among the top-ranked predictions for a significant fraction of mental health indications, demonstrating a significant preference for treating such indications over non-mental health indications, relative to randomized controls (p-value < 10-12). Also, we analyzed the use of specific tryptamines for the treatment of sleeping disorders, bupropion for substance abuse disorders, and cannabinoids for epilepsy. Our innovative use of the CANDO platform may guide the identification and development of novel therapies for mental health indications and provide an understanding of their causal basis on a detailed mechanistic level. These predictions can be used to provide new leads for preclinical drug development for mental health and other neurological disorders. -
Tihkal, the Numbers Are Devoted to the Indole Ring, and the Alpha and Beta Terms to the Side-Chain
Tryptamines i Have Known And Loved: The Chemistry Continues By Alexander and Ann Shulgin trypt-amine \ 'trip-ta-,men \ n. [tryptophan fr. tryptic, fr. trypsin, fr. Gk. tryein, to wear down (from its occurence in pancreatic juice as a proteolytic enzyme) + amine fr. NL ammonia] 1: A naturally occurring compound found in both the animal and plant kingdoms. It is an endogenous component of the human brain. 2: Any of a series of compounds containing the tryptamine skeleton, and modified by chemical constituents at appropriate positions in the molecule. INDEX TO THE TRYPTAMINES # SUBSTANCE CHEMICAL NAME 1 AL-LAD 6-Allyl-N,N-diethyl-NL 2 DBT N,N-Dibutyl-T 3 DET N,N-Diethyl-T 4 DIPT N,N-Diisopropyl-T 5 alpha,O-DMS 5-Methyoxy-alpha-methyl-T 6 DMT N,N-Dimethyl-T 7 2,alpha-DMT 2,alpha-Dimethyl-T 8 alpha,N-DMT alpha,N-Dimethyl-T 9 DPT N,N-Dipropyl-T 10 EIPT N-Ethyl-N-isopropyl-T 11 alpha-ET alpha-Ethyl-T 12 ETH-LAD 6,N,N-Triethyl-NL 13 Harmaline 3,4-Dihydro-7-methoxy-1-methyl-C 14 Harmine 7-Methyoxy-1-methyl-C 15 4-HO-DBT N,N-Dibutyl-4-hydroxy-T 16 4-HO-DET N,N-Diethyl-4-hydroxy-T 17 4-HO-DIPT N,N-Diisopropyl-4-hydroxy-T 18 4-HO-DMT N,N-Dimethyl-4-hydroxy-T 19 5-HO-DMT N,N-Dimethyl-5-hydroxy-T 20 4-HO-DPT N,N-Dipropyl-4-hydroxy-T 21 4-HO-MET N-Ethyl-4-hydroxy-N-methyl-T 22 4-HO-MIPT 4-Hydroxy-N-isopropyl-N-methyl-T 23 4-HO-MPT 4-Hydroxy-N-methyl-N-propyl-T 24 4-HO-pyr-T 4-Hydroxy-N,N-tetramethylene-T 25 Ibogaine A complexly substituted-T 26 LSD N,N-Diethyl-L 27 MBT N-Butyl-N-methyl-T 28 4,5-MDO-DIPT N,N-Diisopropyl-4,5-methylenedioxy-T 29 5,6-MDO-DIPT -
Federal Register/Vol. 71, No. 150/Friday, August 4, 2006/Notices
Federal Register / Vol. 71, No. 150 / Friday, August 4, 2006 / Notices 44315 or more of the following conditions: (a) 4-acetoxy-N,N-diethyltryptamine Signed in Washington, DC, this 28th day of Has a secondary or tertiary amine 5-methoxy-N,N-diallyltryptamine July 2006. formed by the substitution on the 5-methoxy-N-monoallyltryptamine Erica R. Cantor, nitrogen atom of the 2-aminoethyl chain 5-methoxy-N-methyl-N-isopropyltryptamin Director, Division of Trade Adjustment by various alkyl groups, whether in N-methyl-N-isopropyltryptamine Assistance. 4-hydroxy-N,N-diethyltryptamine chain or ring form (for example, N- [FR Doc. E6–12614 Filed 8–3–06; 8:45 am] 5-methoxy-N,N-diethyltryptamine alkyltryptamine, N,N-dialkyltryptamine, BILLING CODE 4510–30–P N,N-tetramethylenetryptamine), (b) has Such information may be submitted to an alkyl substitution on the alpha the Drug and Chemical Evaluation position of the 2-aminoethyl chain, and/ Section and is requested by October 3, DEPARTMENT OF LABOR or (c) has substituents on the indole ring 2006. Information designated as Employment and Training system, including, but not restricted to, confidential or proprietary will be Administration various alkyl chains, halogens, treated accordingly. Confidential hydroxyl, alkoxy, acetyl, or alkylthio business information is protected from [TA–W–58,819] groups, at one or more positions except disclosure under Exemption 4 of the the one (indole nitrogen) position. DEA Freedom of Information Act, 5 U.S.C. Bentwood Furniture, Inc., Grants Pass, is especially interested in learning of the 552(b)(4)(FOIA) and the Department of OR; Affirmative Determinations for uses of the following tryptamines. -
Analytical Methods for Psychoactive N,N-Dialkylated Tryptamines
Trends Trends in Analytical Chemistry, Vol. 29, No. 8, 2010 Analytical methods for psychoactive N,N-dialkylated tryptamines Simon D. Brandt, Cla´udia P.B. Martins Many N,N-dialkylated tryptamine derivatives can induce altered states of human psychoactivity. Most of the cur- consciousness in humans. The term ‘‘hallucinogen’’ is often used when de- rently-known derivatives may show oral scribing the effect on the human mind, and the extent of psychoactivity activity, although homologation of the depends on the nature of substituents attached to the ethylamine side chain N,N-dialkyl chain appears to reduce po- and the indole ring. Naturally-occurring tryptamines (e.g., N,N-dimethyl- tency [1,3]. tryptamine and psilocybin) have increasingly been investigated in human The impact on neurotransmitter systems clinical studies, which increased interest within a number of scientific is incompletely understood but current communities and the public. Many of these derivatives are controlled sub- knowledge indicates an involvement of stances and an increasing number of previously unreported and structurally 5-HT2A and various 5-HT1 receptor sub- modified N,N-dialkylated ‘‘designer’’ tryptamines with unknown bioactive types [4–7]. Interestingly, it was recently profiles have become available. observed that DMT 1 served as an agonist This review provides an overview of analytical methodologies published in at the sigma-1 receptor [8]. In addition, recent years on detection and characterization of 40 N,N-dialkylated deri- DMT and a number of N,N-dialkylated vatives. The majority of literature available utilized reversed-phase high- tryptamines (6, 11 and 12) were also performance liquid chromatography, gas chromatography and/or capillary found to be substrates at both the plasma electrophoresis. -
New Psychoactive Substances (NPS)
New Psychoactive Substances (NPS) LGC Quality Reference ISO 9001 ISO/IEC 17025 ISO Guide 34 materials GMP/GLP ISO 13485 2019 ISO/IEC 17043 Science for a safer world LGC offers the most extensive and up-to-date range of New LGC is a global leader in Psychoactive Substances (NPS) measurement standards, reference materials. reference materials, laboratory services and proficiency testing. With 2,600 professionals working When you make a decision using The challenge The LGC response We are the UK’s in 21 countries, our analytical our resources, you can be sure it’s designated National measurement and quality control based on precise, robust data. And New Psychoactive Substances In response to the ever-expanding LGC Standards provides the widest Measurement services are second-to-none. together, we’re creating fairer, safer, (NPS) continue to be identified, range of NPS being developed, LGC range of reference materials Institute for chemical more confident societies worldwide. and it appears that moves by the has produced a comprehensive available from any single supplier. and bioanalytical As a global leader, we provide the United Nations and by individual range of reference materials that We work closely with leading widest range of reference materials lgcstandards.com countries to control lists of meet the rapidly changing demands manufacturers to provide improved measurement. available from any single supplier. named NPS may be encouraging of the NPS landscape. Many of access to reference materials, the development of yet further these products are produced under with an increasingly large range variants to avoid these controls. the rigorous quality assurance of parameters, for laboratories standards set out in ISO Guide 34. -
Tihkal: the Continuation, by Alexander and Ann Shulgin
The Vaults of Erowid : TiHKAL: The Continuation, by Alexander and Ann Shulgin The existence of Erowid.org is only possible through the support of visitors. Please become a member or make a donation today. Tryptamines i Have Known And Loved: The Chemistry Continues By Alexander and Ann Shulgin trypt-amine \ 'trip-ta-,men \ n. [tryptophan fr. tryptic, fr. trypsin, fr. Gk. tryein, to wear down (from its occurence in pancreatic juice as a proteolytic enzyme) + amine fr. NL ammonia] 1: A naturally occurring compound found in both the animal and plant kingdoms. It is an endogenous component of the human brain. 2: Any of a series of compounds containing the tryptamine skeleton, and modified by chemical constituents at appropriate positions in the molecule. COPYRIGHT NOTICE The Copyright for Part 1 of TiHKAL has been reserved in all forms and it may not be distributed. Part 2 of TiHKAL may be distributed for non-commerical reproduction provided that the introductory material, copyright notice, cautionary notice and ordering information remain http://www.erowid.org/library/books_online/tihkal/tihkal.shtml (1 èç 4) [26.12.02 19:50:57] The Vaults of Erowid : TiHKAL: The Continuation, by Alexander and Ann Shulgin attached. CAUTIONARY NOTE: READ BEFORE PROCEEDING I would like to take a moment to reiterate that at the present time restrictive laws are in force in the United States and it is very difficult for researchers to abide by the regulations which govern efforts to obtain legal approval to do work with these compounds in human beings..... No one who is lacking legal authorization should attempt the synthesis of any of the compounds described in these files, with the intent to give them to man. -
Tryptamine Derivatives by Liquid Chromatography–UV Absorption and –Electrospray Ionization Mass Spectrometry
ANALYTICAL SCIENCES JUNE 2009, VOL. 25 759 2009 © The Japan Society for Analytical Chemistry Simultaneous Separation and Detection of 18 Phenethylamine/ Tryptamine Derivatives by Liquid Chromatography–UV Absorption and –Electrospray Ionization Mass Spectrometry Yao HSIAO,* Ju-Tsung LIU,** and Cheng-Huang LIN*† *Department of Chemistry, National Taiwan Normal University, 88 Sec. 4, Tingchow Road, Taipei, Taiwan **Forensic Science Center, Military Police Command, Department of Defense, Taipei, Taiwan The optimal conditions for the separation and detection of a mixture of 18 phenethylamine/tryptamine derivatives were determined, using liquid chromatography/UV-absorption (LC/UV) and liquid chromatography/electrospray ionization mass spectrometry (LC/ESI MS) methods, respectively. Complete separation could be achieved within ~25 min using gradient elution (A, 0.1% formic acid aqueous solution/pH 2.5; B, acetonitrile). The limit of detection (LOD at S/N = 3) obtained by LC/UV-absorption (absorption wavelength, 280 nm) was in the range from 0.3 to 3 mg/mL. In contrast, when the LC/ESI MS method was used, the LODs for primary, secondary and tertiary amines were in the ranges 0.1 – 3.0, 0.1 – 0.2, and 0.05 – 1.8 mg/mL, respectively. The lower LOD obtained for a tertiary amine can be attributed to the fact that its ionization efficiency (during the ESI process) is better than the others. In order to improve the LOD of a primary/secondary amine, a derivatization procedure was used in which the chemical structure was altered to a secondary/tertiary amine, via a reaction with acetic anhydride. As a result, the LODs for primary/secondary amines could be significantly improved.