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Trigeminal nerve pain can be triggered/worsened by an enlarged vein pushing against the nerve at just the right spot. Cannabis causes hypotension via vasodilation, hence the potential trigger.
The thing is, veins don't grow perfectly parallel, which means hypertension can also cause pain via vasoconstriction, if the vein slightly spirals around the nerve and also constricts; think like a snake wrapped around an arm and squeezing. So it's possible both localized vasodilation and vasoconstriction are causing these headaches, considering the times the headache is worst ("cannabis use or after waking up) and mild but constant (after stimulants like caffeine).
If your pressure is a bit high during the day, a very small dose of a vasodilator drug taken after your medication would normalize it and that would, hopefully, stop the pain overall. You could still have orthostatic blood pressure issues too, but certain mild exercises can help with those too (assuming there's no other underlying blood flow issues).
But there's not enough data to say conclusively, hence taking your blood pressure as directed, as well as throughout the day sitting (after sitting at least 3 minutes without moving much) to see if there's any abnormalities with it, as well as the orthopedic pillow. If the pillow helps it also narrows down the cause.
That said, if it's the trigeminal nerve and you can't control the veins there well through medication... Good luck I suppose. Most surgeons won't want to cauterize because of mild (yet constant) pain. Acupuncture could achieve the same result, but that would be a scary gamble, because there's also potential they hit the nerve wrong with the micro needle and instead worsen the pain. That would be a last result solution, assuming it's the trigeminal nerve causing you issues.
Forgot to mention, don't know where you live, but Omron makes good enough yet affordable blood pressure machines. Just don't ever get anything for the wrist.
But caffeine is not causing any headaches. Did I accidentally imply that somewhere? It's rather enhancing the painkiller's effect. In fact, a few times I drank around 14 espressos just for fun and curiosity, and I never got any headaches. Although, normally, if I don't also drink a glass of water immediately afterwards, I have a reasonable chance of developing a headache, which is not due to dehydration, oddly enough, because drinking other hydrating substances (like milk in the coffee) does not help; It has to be water. Another reason to think this is that the headache can already start a few minutes in, which is way too fast for dehydration to happen.
I know this doesn't add any value (and probably only confusion), but taking coffee at certain times, as well as sugar and other kind of (especially processed) foods, does indeed lead to headaches, but these moments are just random moments during the day (or week) which I can only just intuitively feel; so I can feel when they are 'at play', it's like I'm just more 'vulnerable' to certain substances at these moments. That's the only difference. Took me years to realize. I know this sounds wacky as hell. Way too weird and vague. Especially considering I have no allergies or any other medical condition whatsoever (same for family members). (Yes perhaps ADHD but even I doubt that to some extend.) So perhaps best to ignore this last paragraph, because I don't know what to make of it, except being just sensitive.
I'm living in west europe. These blood pressure machines are actually not that expensive. God, I feel stupid to not have searched for this sooner. I even see the Omron devices for ~70 euros. I'm in great student loan debt but I'll gladly make room for this device
I did misunderstand about the association with the caffeine and your headache. But if anything, the new information provided, along with what you mentioned about water, narrows it down further to you potentially having some form of hypotension.
You very are likely dehydrated btw. Milk and juice are not hydrating - milk is only 88% water, but the sugars and fats included in the milk reduce how much of that water your body absorbs. Likewise many juices have so much sugar that it also lowers how much water to get from it in your gut, and if your blood glucose is already high it hydrates you even less. Speaking of, have you ever done a glucose test at a doctors? Either way, water would be your best option.
Coffee is a natural diuretic, meaning it dehydrates you faster as well. Dehydration causes hypotension as well (although in rare cases, such as me and my mother, you can experience paradoxical effects, just to keep in mind).
High blood glucose levels and unstable blood pressure are not commonly obvious medical conditions, which is why they're annoying.
If you have doubts about your ADHD, speak with your doctor (not a psychologist) about it. You can also do some comparative tests on yourself (when on vacation of some sort) of before and after. Take such a test while on your medication, and then wait 3 weeks (to make sure your body is fully clear of the medication) then do such a test again (not the exact same test though). If there's significant deviation, then you should probably keep taking the medication, but if there isn't, then maybe talk with a doctor about it.
It's important you don't quit a medication such as Ritalin at once though, so the titration schedule should look something like this:
Day 1✓ 2× 3✓ 4× 5✓ 6× 7× 8✓ 9× 10× 11✓ 12+ stop
Disclaimer: I'm not a doctor, just someone with a lot of medical knowledge from self study from medical and pharmacological text books due to my and family members medical conditions. I recommend to a doctor first and foremost, but used to live in the USA, where going as needed is not financially viable for many, even with great insurance.
Lastly, if you shop around, you might find a good Omron device even cheaper on sale, if you're on a budget. Even they're basic models are well enough, since they are actually medically calibrated on good data sets.
I've been drinking a lot more water the last 5 years which lessened the headaches a little bit. But tbh, I think I drink enough water actually, hard to say exactly how much, but at least before bed (quite) a few glasses of water. During the day (when outdoors) I could probably drink more water, but my body fairly readily produces a lot of urine, or I just have a small bladder, but I'm more inclined to the former one. But waking up with a headache caused by dehydration is unlikely due to drinking the night before bed. I varied the amount of water, but had little effect, except needing to go to the bathroom 5 times before falling asleep. (Not that the water is holding me back from sleeping, but I usually read in bed 1-2 hours, so my kidneys start doing their thing. On that note, reading posture is also unlikely a cause since I only started reading recently (~few years).)
I sometimes do eat a lot of candy (and have throughout my life), but still, even with many months of abstaining from it, there was no difference in headaches. I did not ever take any glucose test. (I once almost did.)
The ADHD diagnosis and med are still relative recent things (~since start of 2024). I'm still experimenting with the meds, what their exact effects are on me, etc. I think they make my head a bit more calm, empty, relaxed, but idk yet, I'm skeptical and cynic of everything until I have tested it thoroughly. I've been on and off of the meds, actually... The psychiatrist said it was ok to do this. But whatever, they're more here to help me study, rather then help me in life.