A foxy intoxication

Wilson, John; McGeorge, Frank; Smolinske, Susan C.; Meatherall, Robert

doi:10.1016/j.forsciint.2004.04.017

Cited by 117 publications

(56 citation statements)

References 5 publications

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“…DALT 0.14-1.7 (Elliott and Evans, 2014;Tanaka et al, 2006;Wilson et al, 2005) 0.6-7.1 0.4 (± 0.1) 175 (± 105) 2.6 (± 2) 91(± 12) 90 (± 12)…”

Section: Dalt-typementioning

confidence: 99%

“…0.14-1.7 (Elliott and Evans, 2014;Tanaka et al, 2006;Wilson et al, 2005) 0.5-6. 5-Br-DALT 0.14-1.7 (Elliott and Evans, 2014;Tanaka et al, 2006;Wilson et al, 2005) 0.4-5.3 0.8 (± 0.2) 52 (± 0.6) 176 (± 15) 23 (± 0.04) 52 (± 3.4) 2.5 (± 0.4) 122 (± 58) 60 (± 16) 5-Me-DALT 0.14-1.7 (Elliott and Evans, 2014;Tanaka et al, 2006;Wilson et al, 2005) 0.6-6.7 0.7 (± 0.5) 138 (± 14) 77 (± 13) 156 (± 3.4) 3.8 (± 0.7) 11 (± 12) 67 (± 9.8)…”

Section: -Cl-daltmentioning

confidence: 99%

“…0.14-1.7 (Elliott and Evans, 2014;Tanaka et al, 2006;Wilson et al, 2005) 0.5-6.3 0.4 (± 0.1) 0.8 (± 0.9) 111 (± 128) 13 (± 11) 20 (± 14) 114 (± 36) 6-F-DALT 0.14-1.7 (Elliott and Evans, 2014;Tanaka et al, 2006;Wilson et al, 2005) 0. 7-Me-DALT 0.14-1.7 (Elliott and Evans, 2014;Tanaka et al, 2006;Wilson et al, 2005) 0.6-6.7 0.1 (± 0.03) 5,6-MD-DALT (Dinger et al, 2014c) 0.14-1.7 (Elliott and Evans, 2014;Tanaka et al, 2006;Wilson et al, 2005) 0.5-6 0.3 (± 0.2) 26 (± 15) 58 (± 0.7) 58 (± 17) 0.4 (± 0.3) 15 (± 0.1)…”

Section: -Meo-daltmentioning

confidence: 99%

“…The class of N,N-dialkylated tryptamines has been a constant element of interest within the context of new psychoactive substances (NPS) (Meatherall and Sharma, 2003;Smolinske et al, 2005;Tanaka et al, 2006;Vorce and Sklerov, 2004;Wilson et al, 2005). Another newer tryptamine, 5-methoxy-N,N-diallyltryptamine (5-MeO-DALT), was associated with a fatal poisoning (Elliott and Evans, 2014).…”

Section: Introductionmentioning

confidence: 99%

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Cytochrome P450 inhibition potential of new psychoactive substances of the tryptamine class

et al. 2016

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R., Maurer, Hans H., Cytochrome P450 inhibition potential of new psychoactive substances of the tryptamine class.Toxicology Letters http://dx.doi.org/10.1016/j.toxlet. 2015.11.013 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.  IC50 values were comparable to that of clinically relevant inhibitors. Members of the DALT family were strong inhibitors of CYP1A2 and CYP2D6 activity. 5-MeO-DALT showed in vivo inhibition against CYP1A2 activity. ABSTRACTNew psychoactive substances (NPS) are not tested for their cytochrome P450 (CYP) inhibition potential before consumption. Therefore, this potential was explored for tryptamine-derived NPS (TDNPS) including alpha-methyl tryptamines (AMTs), dimethyl tryptamines (DMTs), diallyl tryptamines (DALTs), and diisopropyl tryptamines (DiPTs) using test substrates preferred by the Food and Drug Administration in a cocktail assay. All tested TDNPS with the exception of DMT inhibited CYP2D6 activity with IC50 values below 100 µM. DALTs inhibited CYP2D6 activity similar to paroxetine and quinidine and CYP1A2 activity comparable to fluvoxamine. 5-Methoxy-N,N-diallyltryptamine reduced in vivo the caffeine metabolism in rats consistent with in vitro results. Five of the AMTs also inhibited CYP1A2 activity comparable to amiodarone. AMT and 6-F-AMT inhibited CYP2A6 activity in the range of the test inhibitor tranylcypromine. CYP2B6 activity was inhibited by 19 tryptamines, but weakly compared to efavirenz. CYP2C8 activity was inhibited by five of the tested TDNPS and three showed values comparable to trimethoprim and gemfibrozil. Six tryptamines inhibited CYP2C9 and seven CYP2C19 activities comparable to fluconazole and chloramphenicol, respectively. Nineteen compounds showed inhibition of CYP2E1 and 18 of CYP3A activity, respectively. These results showed that the CYP inhibition by TDNPS might be clinically relevant, but clinical studies are needed to explore this further.

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“…DALT 0.14-1.7 (Elliott and Evans, 2014;Tanaka et al, 2006;Wilson et al, 2005) 0.6-7.1 0.4 (± 0.1) 175 (± 105) 2.6 (± 2) 91(± 12) 90 (± 12)…”

Section: Dalt-typementioning

confidence: 99%

Section: -Cl-daltmentioning

confidence: 99%

Section: -Meo-daltmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Cytochrome P450 inhibition potential of new psychoactive substances of the tryptamine class

et al. 2016

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“…5-MEO-DIPT was first synthesized by Shulgin and Carter (1980) and was described as inducing auditory and visual hallucinations in humans lasting 3-6 h. Emergency room reports and recent case studies confirm the auditory and visual hallucinogenic properties of 5-MEO-DIPT and suggest that the drug can also produce tactile hallucinations, agitation, tachycardia, somatic disturbance, cataleptic states, unconsciousness, flashbacks, increased glucose levels, vomiting, rhabdomyolysis, and in at least one case, seizure activity or death (Alatrash et al, 2006;Ikeda et al, 2005;Kiyota, 2004;Meatherall and Sharma, 2003;Muller, 2004;Smolinske et al, 2004;Tanaka et al, 2006;Wilson et al, 2005). From case studies, users have reported administering various amounts of the drug (ie, 10-37.5 mg) via oral or rectal routes of administration (Ikeda et al, 2005;Kiyota, 2004).…”

Section: Introductionmentioning

confidence: 99%

Alterations in Body Temperature, Corticosterone, and Behavior Following the Administration of 5-Methoxy-Diisopropyltryptamine (‘Foxy’) to Adult Rats: a New Drug of Abuse

Williams

Herring

Schaefer

et al. 2006

Neuropsychopharmacol

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Many drugs are used or abused in social contexts without understanding the ramifications of their use. In this study, we examined the effects of a newly popular drug, 5-methoxy-diisopropyltryptamine (5-MEO-DIPT; 'foxy' or 'foxy-methoxy'). Two experiments were performed. In the first, 5-MEO-DIPT (0, 10, or 20 mg/kg) was administered to rats four times on a single day and animals were examined 3 days later. The animals that received 5-MEO-DIPT demonstrated hypothermia during the period of drug administration and delayed mild hyperthermic rebound for at least 48 h. Corticosterone levels in plasma were elevated in a dose-dependent manner compared to saline-treated animals with minor changes in 5-HT turnover and no changes in monoamine levels. In experiment 2, rats were examined in behavioral tasks following either 0 or 20 mg/kg of 5-MEO-DIPT. The animals treated with 5-MEO-DIPT showed hypoactivity and an attenuated response to ( + )-methamphetamine-induced stimulation (1 mg/kg). In a test of path integration (Cincinnati water maze), 5-MEO-DIPT-treated animals displayed deficits in performance compared to the saline-treated animals. No differences were noted in the ability of the animals to perform in the Morris water maze or on tests of novel object or place recognition. The data demonstrate that 5-MEO-DIPT alters the ability of an animal to perform certain cognitive tasks, while leaving others intact and disrupts the endocrine system. 5-MEO-DIPT may have the potential to induce untoward effects in humans.

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Tryptamine Designer Drugs

2012

Medical Toxicology of Drug Abuse

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A foxy intoxication

Cited by 117 publications

References 5 publications

Cytochrome P450 inhibition potential of new psychoactive substances of the tryptamine class

Cytochrome P450 inhibition potential of new psychoactive substances of the tryptamine class

Alterations in Body Temperature, Corticosterone, and Behavior Following the Administration of 5-Methoxy-Diisopropyltryptamine (‘Foxy’) to Adult Rats: a New Drug of Abuse

Tryptamine Designer Drugs

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