EWS_EU: neue psychoaktive Substanzen
andrea.bodenwinkler
#1 Geschrieben : Mittwoch, 1. April 2015 12:52:34(UTC)
Rang: Advanced Member

Beiträge: 213

Sehr geehrte Fachleute!

Anbei leiten wir Ihnen die aktuellsten Informationen der EMCDDA zu neuen psychoaktiven Substanzen weiter.

In Schweden wurden zwei neue psychoaktive Substanzen identifiziert.

1) Naphthalen-1-yl-1-pentyl-1H-indazole-3- carboxylate (SDB-005): The substance is a synthetic cannabinoid and is structurally related to PB-22. SDB-005 is the indazole analogue of PB-22 where the 8-hydroxyquinoline has been replaced with a naphthalene group. Research evaluating the pharmacology of adamantane-derived indoles reported that SDB-005 showed a preference for CB1 receptors (CB1 EC50=21 nM, CB2 EC50=140 nM) [1]. SDB-005 was identified in a seizure of 99.7 grams of pale beige powder by Swedish Customs on the 18 February 2015 in Stockholm. The substance was analytically confirmed by GC-MS, FT-IR and NMR at the Swedish National Forensic Centre.

2) N-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(5-fluoropentyl)-1H-indazole-3-carboxamide (5F-ADB-PINACA): The substance is a synthetic cannabinoid and is the 5-fluoro derivative (fluorinated at the end of the N-pentyl chain) of ADB-PINACA . An alert was issued by the EWS on ADB-PINACA in March 2014 and this substance is structurally related to AKB-48/APINACA, in which the adamantyl ring system has been replaced by 1-amino-3,3-dimethyl-1-oxobutan-2-yl (ADB). 5F-ADB-PINACA was identified in a seizure of 5.04 grams of plant material by Swedish Police on the 18 February 2015 in Piteå. The substance was analytically confirmed by GC-MS, LC-MS, GC-IRD and NMR at the Swedish National Forensic Centre.
References:
[1]. Banister, S. D., Wilkinson, S. M., Longworth, M., Stuart, J., Apetz, N., English, K., ... & Kassiou, M. (2013). The synthesis and pharmacological evaluation of adamantane-derived indoles: cannabimimetic drugs of abuse. ACS chemical neuroscience, 4(7), 1081-1092


In Dänemark wurde die neue psychoaktive Substanz (6aR,9R)-7-allyl-N,N-diethyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide (AL-LAD) identifiziert.

AL-LAD (also known as 6-allyl-6-nor-lysergic acid diethylamide, 6-allyl-6-nor-LSD) is sold as LaSiDium by some online vendors and this is a synthetic substance categorised as a lysergamide. AL-LAD is structurally related to lysergic acid diethylamide (LSD) but differs in the replacement of the methyl group with an allyl group at the 6th nitrogen. AL-LAD is described in Alexander and Ann Shulgin's book Triptamines I Have Known and Loved (TiHKAL) as entry number 1, where the starting material is stated as nor-LSD [1]. A dosage of 80-160 micrograms and a duration of action of six to eight hours is also described [1]. At a dosage of 160 micrograms a user self-report comments that "there was some visual distortion similar to LSD" [1]. The synthesis and LSD-like stimulus properties of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives has been reported [2]. AL-LAD was identified in a seizure of 4 beige blotters by Danish Customs at the Copenhagen International Post Office on the 7 January 2015. The substance was analytically confirmed by GC-MS. AL-LAD was reported by the United Kingdom National Focal Point at the beginning of 2014 after it was identified in a collected sample of a paper tab purchased online in October 2013, however it was not formally notified as analytical data was not provided. AL-LAD is now controlled in the United Kingdom under the Misuse of Drugs Act 1971 [3].
References:
[1]. Tihkal - The Continuation, Alexander and Ann Shulgin, Transform Press, 1997.
[2]. Hoffman, A. J., & Nichols, D. E. (1985). Synthesis and LSD-like discriminative stimulus properties in a series of N (6)-alkyl norlysergic acid N, N-diethylamide derivatives. Journal of medicinal chemistry, 28(9), 1252-1255.
[3]. https://www.gov.uk/gover...nd-rescheduling-of-ghb.


In Holland wurde die neue psychoaktive Substanz 1-((2,2-difluorobenzo[D][1,3]dioxol-5-yl)methyl)piperazine (DB-MDBP) identifiziert.

DB-MDBP is a piperazine derivative structurally related to BZP and MDBP (1-(3,4-methylenedioxybenzyl)piperazine). MDBP is the methylenedioxy derivative of BZP and DB-MDBP differs from MDBP in that it also contains two fluorine atoms attached to the methylenedioxy group. It has been reported that due to the structural similarity between MDBP and BZP, amphetamine-like effects could be likely [1]. DB-MDBP was identified in a seizure of 17.0 grams of powder by Dutch Customs in 2015. The substance was analytically confirmed by GC-MS, FT-IR, LC-MS and NMR at the Dutch Customs Laboratory.
[size=3
]References:
[1]. Staack, R. F. and Maurer, H. H. (2004), New designer drug 1-(3,4-methylenedioxybenzyl) piperazine (MDBP): studies on its metabolism and toxicological detection in rat urine using gas chromatography/mass spectrometry. J. Mass Spectrom., 39: 255–261. doi: 10.1002/jms.556
[/size]

In Polen wurde die neue psychoaktive Substanz 1-(4-bromophenyl)-2-pyrrolidin-1-yl-pentan-1-one (4Br-α-PVP) identifiziert.

4Br-α-PVP is a synthetic cathinone and is structurally related to α-PVP and 4F-α-PVP, where there is substitution at position 4 on the phenyl ring with a bromine atom. The synthesis of 4Br-α-PVP is described by Meltzer et al., (compound 4f) [1]. 4Br-α-PVP was identified in a seizure of 30 milligrams of white powder in Krakow on the 31st of July 2013 by the Prosecuting Authority. The substance was analytically confirmed by LC-MS/MS-TOF, GC-MS/MS and NMR by the National Medicines Institute in Warsaw.
References:
[1]. Meltzer PC, Butler D, Deschamps JR, Madras BK (2006) 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (Pyrovalerone) Analogues: A Promising Class of Monoamine Uptake Inhibitors. Journal of Medicinal Chemistry 49, 1420-1432.


In Estland wurde die neue psychoaktive Substanz 2-benzhydrylsulfonylacetamide (Modafinil sulphone)identifiziert.

Modafinil sulphone (also known as 2-[(diphenylmethyl)sulfonyl]acetamide; CRL 41056 and USP Modafinil Related Compound B [1]) is considered to be one of two metabolites of modafinil, it being the minor metabolite [2,3]. Modafinil is a wakefulness-promoting medication used in the treatment of narcolepsy, shift work sleep problems and obstructive sleep apnea. Modafinil sulphone is structurally related to the previously notified modafiendz, which is the bis-fluoro-N-methyl analogue of modafinil. The properties of modafinil sulphone have not been described extensively in the literature. It has been reported that this substance has anticonvulsant activity and therefore may find use in the "treatment of preclinical subconvulsive manifestations", further studies are required in this area [4,5]. In other research, it has been stated that modafinil sulphone is pharmacologically active with a half-life of approximately 12 hours but it has been reported that it may also not exert any significant activity in the brain or periphery [6,7]. Modafinil sulphone was identified in a seizure of 98.77 grams of white powder seized on the 19 May 2014 by Estonian Customs in Tallinn. The substance was detected in a package sent in the post from China. The substance was analytically confirmed by FTIR and HPLC-MS by the Estonian Forensic Science Institute.
References:
[1]. http://trc-canada.com/de...15H15NO3S&Synonym=2-[%28Diphenylmethyl%29sulfonyl]acetamide;%202-%28Benzhydrylsulfonyl%29acetamide;%20CRL%2041056;
[2]. McClellan, K. J., & Spencer, C. M. (1998). Modafinil. CNS drugs, 9(4), 311-324
[3]. Robertson Jr, P., & Hellriegel, E. T. (2003). Clinical pharmacokinetic profile of modafinil. Clinical pharmacokinetics, 42(2), 123-137
[4]. Chatterjie, N., Stables, J. P., Wang, H., & Alexander, G. J. (2004). Anti-narcoleptic agent modafinil and its sulfone: a novel facile synthesis and potential anti-epileptic activity. Neurochemical research, 29(8), 1481-1486
[5]. Zolkowska, D., Andres-Mach, M., Prisinzano, T. E., Baumann, M. H., Luszczki, J. J. Modafinil and its metabolites enhance the anticonvulsant action of classical antiepileptic drugs in the mouse maximal electroshock-induced seizure model. Psychopharmacology, DOI 10.1007/s00213-015-3884-3.
[6]. Wesensten, N. J. (2006). Effects of modafinil on cognitive performance and alertness during sleep deprivation. Current pharmaceutical design, 12(20), 2457-2471
[7]. Minzenberg, M. J., & Carter, C. S. (2008). Modafinil: a review of neurochemical actions and effects on cognition. Neuropsychopharmacology, 33(7), 1477-1502

Sollten zu den genannten Substanzen Informationen aus Österreich vorliegen, bitten wir um Weiterleitung an ews@goeg.at.

Mit freundlichen Grüßen
Andrea Bodenwinkler


Informations – und Frühwarnsystem über besondere Gesundheitsgefahren im Zusammenhang mit Substanzkonsum
Aktuelle Informationen und Warnungen: https://forum.goeg.at/ewsforum/


Dr. Andrea Bodenwinkler
Gesundheit Österreich GmbH
Stubenring 6
1010 Wien
T: +43 1 515 61-187
F: +43 1 513 84 72
andrea.bodenwinkler@goeg.at
www.goeg.at
ews@goeg.at
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