Wikipedia:Reference desk/Archives/Science/2021 March 20

= March 20 =

Resisting interrogation
If you are being subjected to interrogation with the use of a truth serum, is it possible to consciously resist it by using some kind of mind tricks (as described, for example, in Licence Renewed by Ian Fleming)? Or is that complete rubbish? 2601:646:8A01:B180:8D26:95C8:721A:5EF0 (talk) 06:54, 20 March 2021 (UTC)
 * The article you linked says, "There is currently no drug proven to cause consistent or predictable enhancement of truth-telling." So it leans toward the "rubbish" end of the spectrum. ←Baseball Bugs What's up, Doc? carrots→ 07:11, 20 March 2021 (UTC)


 * Truth serums aren't a magic "they give you the shot and now you're incapable of lying" kind of thing like fiction often depicts them. As the article says, "There is currently no drug proven to cause consistent or predictable enhancement of truth-telling." Rather, they lower your inhibitions in a manner similar to alcohol. Thus, they also come with unpredictability and significant person-to-person variations. I couldn't say how a truth serum would exactly affect you, and that effect might be very different from how it might affect me. My advice is just avoid any getting captured by the KGB in the first place. TheMrP (talk) 07:17, 20 March 2021 (UTC)


 * It's also worth pointing out that the article you linked says, "There is currently no drug proven to cause consistent or predictable enhancement of truth-telling." Your IP geolocates to California, so you're probably safe from the KGB, but you never know. ←Baseball Bugs What's up, Doc? carrots→ 09:24, 20 March 2021 (UTC)


 * Just to repeat: my question is not whether the use of a truth serum is a reliable interrogation technique (it's not, and I already knew that), my question is whether there exist techniques for a subject to consciously resist such an interrogation! 2601:646:8A01:B180:8D26:95C8:721A:5EF0 (talk) 09:52, 20 March 2021 (UTC)
 * TheMrP's response contains your answer: It's going to depend on the individual. ←Baseball Bugs What's up, Doc? carrots→ 10:25, 20 March 2021 (UTC)
 * No. There is still the unanswered question of whether (variability of effects between individuals aside) the CIA, for instance, ever developed training which could allow their agents to consistently resist such interrogations.  I don't know the answer to that, but I did just fix the "Truth" Drugs in Interrogation dead-link reference (and external link) in our article, adding this link to the archived copy of that CIA release.  I haven't read it to see if it explicitly addresses the question, but our questioner may wish to peruse it.   (It's multi page; see the "Next" and "Previous" links.) -- ToE 13:12, 20 March 2021 (UTC)
 * As usual, Wikipedia has a specific article (albeit short) namely Resistance to interrogation. Mike Turnbull (talk) 13:46, 20 March 2021 (UTC)


 * "Possibly the most effective way to arm oneself against narcointerrogation would be to undergo a "dry run." A trial drug interrogation with output taped for playback would familiarize an individual with his own reactions to "truth" drugs, and this familiarity would help to reduce the effects of harassment by the interrogator before and after the drug has been administered", referring to the tendency of a subject to yield to the mere threat of drug interrogation, or to have an exaggerated impression of how much he has revealed while drugged.
 * Most broadly, there is evidence that drugs have least effect on well-adjusted individuals with good defenses and good emotional control, and that anyone who can withstand the stress of competent interrogation in the waking state can do so in narcosis".
 * "Truth" Drugs in Interrogation, CIA Historical Review Program (pp. 17-18) Alansplodge (talk) 15:03, 20 March 2021 (UTC)
 * Also apologies to ToE who I now see has already linked the same article above. Alansplodge (talk) 15:06, 20 March 2021 (UTC)
 * Thanks! The current location of a PDF is much better than a multi-page archive link.  I've updated the refs and external link in our Truth serum article. -- ToE 15:57, 20 March 2021 (UTC)
 * Without even resorting to more exotic drugs, one could conduct an experiment capturing behavior after having several strong drinks. Some folks get chatty or loose-lipped, others get very quiet. ←Baseball Bugs What's up, Doc? carrots→ 20:04, 20 March 2021 (UTC)
 * Thanks! So it is possible for most people, but each individual has to come up with his/her own resistance method -- is that it?  (Also, just an observation -- the "dry run" suggestion is very much like what pilots do in training when learning to detect the symptoms of hypoxia (which also vary between individuals, and also resemble drunkenness in some ways) -- so it makes perfect sense!) 2601:646:8A01:B180:3938:6001:4113:6130 (talk) 09:24, 21 March 2021 (UTC)

SMILES for intramolecular hydrogen bonds
I am looking for SMILES codes of molecules that form an intramolecular hydrogen bond, especially for phenolic benzotriazoles (see e.g. 10.1016/j.dyepig.2020.108672). I would like to feed these SMILES codes to EPI Suite. --Leyo 10:08, 20 March 2021 (UTC)
 * One interesting case is 2,2'-Dipyrromethene with possible SMILES c1cc([nH]c1)C=C2C=CC=N2 . I don't know of a SMILES bond symbol to indicate a hydrogen bond though. Coding your molecules in that paper to SMILES I get N1=c2ccccc2=NN1c3cc(O)c(O)cc3O and N1=c2ccccc2=NN1c3cc(O)c(O)cc3N where your R and R' will be substed onto the (O) or final N. But it is probably better to ask at Wikipedia talk:WikiProject Chemistry. Graeme Bartlett (talk) 11:03, 20 March 2021 (UTC)
 * SMILES and other structural coding systems such as InChI and Wiswesser line notation do not incorporate hydrogen bonds, they only encode the non-hydrogen framework of the compound. I think that your best bet is to use Chemspider and draw in a simple case such as the first example in the article for phenolic benzotriazoles. Then you can use its interface to do a sub-structure search for molecules of this type. Every molecule in the Chemspider database has the SMILES code available (in the drop-down that says "More details:"). Alternatively, you could use a chemical drawing package (see Manual of Style/Chemistry/Structure drawing). All the main ones can convert drawn structures to SMILES and vice-versa. Contact me on my Talk Page if you need further advice. Incidentally, having an internal hydrogen bond is quite common. Aspirin is an example. Mike Turnbull (talk) 11:29, 20 March 2021 (UTC)
 * I followed your recommendation and used ChemSpider to obtain the (standard) SMILES code of the first example in the article on phenolic benzotriazoles, i.e. UV-P:  Then, I adapted Graeme's SMILES code above for the same substance:
 * BTW: These SMILES codes are converted to identical structural formulas by ACD/ChemSketch and the SMILES generator / checker.
 * When used as an input to EPI Suite, I got higher water solubility estimates for the latter, i.e. the one that is intended to have an intramolecular hydrogen bond. As this is the opposite as what is expected, I assume that EPI Suite does not interpret the latter SMILES code as intended. Please note that contrary to usually, no structural formula is shown. --Leyo 00:27, 21 March 2021 (UTC)
 * Some programs that process SMILES strings do or don't handle aromaticity or resonance in a chemically sane or consistent way. It's a deficiency of programs and somewhat of SMILES. There have actually be edit-wars on enwiki about whether we should use capital letters vs lower-case letters where "we know" there's aromatic nature ("we should be chemically as correct as possible") but some editors report that some parsers can't cope with it ("we should be as universally usable as possible"). DMacks (talk) 04:13, 21 March 2021 (UTC)
 * Difference in solubility would be expected if you vary the "R"s the (O) in the SMILES indicates a hydroxy group, which is quite soluble. But the R may not be a hydrogen, it might be a hydrophobic chain, so you could try (OCCCC) to get butoxy, or other side chains. Graeme Bartlett (talk) 04:46, 21 March 2021 (UTC)
 * It doesn't surprise me that the solubility estimates are different when different (but equivalent) SMILES strings are used for input. The methodology used by the EPI suite involves fragment-based calculations and so it is a bit random how it works out what fragments it should add up and I don't think it ever considers intramolecular H-bonds. Relying on calculations like these is dangerous if you really need to know an accurate value: the output can also depend on the training set. Mike Turnbull (talk) 12:11, 21 March 2021 (UTC)
 * I am not interested in comparing solubility differences for different substitutes but the difference of whether or not the formation of an intramolecular hydrogen bond is considered (what has a big impact on the solubility).
 * The outcome may well be that there is no way to have intramolecular hydrogen bonds considered properly by EPI Suite. --Leyo 23:11, 21 March 2021 (UTC)

Algae in the Sargasso Sea
When approximately algae started accumulating in the Sargasso Sea? Did their buildup roughly coincide with the formation of oceanic gyre in that region, possibly millions years ago? 212.180.235.46 (talk) 22:50, 20 March 2021 (UTC)
 * As a guess, probably with the closing of the Isthmus of Panama 2.8 mya. This made the Gulf Stream take its present course. There may have been different gyres with roughly the same assemblage of organisms starting in the Miocene; researchers are looking at fossils and evolutionary divergence times of Globorotalia and other foraminiferans. Abductive  (reasoning) 18:21, 22 March 2021 (UTC)